GB414452A - The manufacture of asymmetrical thiourea-derivatives - Google Patents
The manufacture of asymmetrical thiourea-derivativesInfo
- Publication number
- GB414452A GB414452A GB732933A GB732933A GB414452A GB 414452 A GB414452 A GB 414452A GB 732933 A GB732933 A GB 732933A GB 732933 A GB732933 A GB 732933A GB 414452 A GB414452 A GB 414452A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrochloride
- thiourea
- derivatives
- ethyl
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001412 amines Chemical class 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- QGLYTNIXHPCRCF-UHFFFAOYSA-N (4-ethoxyphenyl)thiourea Chemical compound CCOC1=CC=C(NC(N)=S)C=C1 QGLYTNIXHPCRCF-UHFFFAOYSA-N 0.000 abstract 2
- VXLFMCZPFIKKDZ-UHFFFAOYSA-N (4-methylphenyl)thiourea Chemical compound CC1=CC=C(NC(N)=S)C=C1 VXLFMCZPFIKKDZ-UHFFFAOYSA-N 0.000 abstract 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 2
- -1 8-chloroquinolyl Chemical group 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003585 thioureas Chemical class 0.000 abstract 2
- UUYSTZWIFZYHRM-UHFFFAOYSA-N (9-ethylcarbazol-3-yl)azanium;chloride Chemical compound [Cl-].[NH3+]C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 UUYSTZWIFZYHRM-UHFFFAOYSA-N 0.000 abstract 1
- KIJJAHDWPAWNGH-UHFFFAOYSA-N 1-ethyl-1-naphthalen-1-ylthiourea Chemical compound C1=CC=C2C(N(C(N)=S)CC)=CC=CC2=C1 KIJJAHDWPAWNGH-UHFFFAOYSA-N 0.000 abstract 1
- FDBKFYGFUMPIAA-UHFFFAOYSA-N 1h-indazol-4-amine;hydrochloride Chemical compound Cl.NC1=CC=CC2=C1C=NN2 FDBKFYGFUMPIAA-UHFFFAOYSA-N 0.000 abstract 1
- JWDHUQFIBCVYRH-UHFFFAOYSA-N 4-methylaniline;sulfuric acid Chemical compound OS(O)(=O)=O.CC1=CC=C(N)C=C1 JWDHUQFIBCVYRH-UHFFFAOYSA-N 0.000 abstract 1
- MAIZCACENPZNCN-UHFFFAOYSA-N 6-amino-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(N)=CC=C21 MAIZCACENPZNCN-UHFFFAOYSA-N 0.000 abstract 1
- KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 abstract 1
- DZWTXWPRWRLHIL-UHFFFAOYSA-N 6-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2N=C(N)SC2=C1 DZWTXWPRWRLHIL-UHFFFAOYSA-N 0.000 abstract 1
- FTIJBSGQFJZPRH-UHFFFAOYSA-N 8-chloroquinolin-5-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(N)=CC=C(Cl)C2=N1 FTIJBSGQFJZPRH-UHFFFAOYSA-N 0.000 abstract 1
- JABZLPUGHKHHIJ-UHFFFAOYSA-N 9h-carbazol-2-amine;hydrochloride Chemical compound [Cl-].C1=CC=C2C3=CC=C([NH3+])C=C3NC2=C1 JABZLPUGHKHHIJ-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KJDKFIOYOQEMCJ-UHFFFAOYSA-N Cl.COC=1C=CC=C2C=CC=C(C12)N Chemical compound Cl.COC=1C=CC=C2C=CC=C(C12)N KJDKFIOYOQEMCJ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 abstract 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- JEFJSEIUEJBMSR-UHFFFAOYSA-N hydron;n-phenylaniline;chloride Chemical compound Cl.C=1C=CC=CC=1NC1=CC=CC=C1 JEFJSEIUEJBMSR-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- CZPDZIFRRRQSHM-UHFFFAOYSA-N n-ethylnaphthalen-1-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(NCC)=CC=CC2=C1 CZPDZIFRRRQSHM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 150000007979 thiazole derivatives Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Thiourea derivatives of the formula R1R2NCSNH2, where R1 is an aryl group and R2 is hydrogen or an alkyl or aryl group, are prepared by heating mineral acid salts of amines of the formula R1R2NH with an alkali thiocyanate or ammonium thiocyanate in the presence of an inert organic diluent. The mineral acid salt of the amine may be prepared in situ, for example by adding sulphuric acid or gaseous hydrogen chloride to a mixture of the amine with the organic diluent. The thiourea derivatives may be converted in known manner into thiazole derivatives without intermediate isolation. Examples are given of the preparation of phenylthiourea from aniline hydrochloride; 4-ethoxyphenylthiourea from p-phenetidine hydrochloride or sulphate; p-tolythiourea from p-toluidine sulphate; asym. diphenylthiourea from diphenylamine hydrochloride; asym. ethyl-1-naphthylthiourea from N-ethyl-1-naphthylamine hydrochloride; 8-methoxynaphthyl-1-thiourea from 8-methoxy-1-naphthylamine hydrochloride; indazyl-4-thiourea from 4-aminoindazole hydrochloride; 1 : 5-naphthylenedithiourea from 1 : 5-naphthylenediamine hydrochloride; carbazyl-2-thiourea from 2-aminocarbazole hydrochloride; 9 - ethylcarbazyl - 3 - thiourea from 9 - ethyl - 3 - aminocarbazole hydrochloride; and 8-chloroquinolyl - 5 - thiourea from 8 - chloro - 5 - amino - quinoline hydrochloride; in each example the amine salt is heated to 90--130 DEG C. with sodium or ammonium thiocyanate in the presence of an organic diluent, which may be chlorobenzene, o-dichlorobenzene, benzine, or butyl alcohol. 4-Ethoxyphenylthiourea obtained as described above may be treated, without isolation, with disulphur dichloride to form 2-amino-6-ethoxybenzothiazole; similarly, p - tolylthiourea obtained as described above may be treated with bromine or sulphuryl chloride to form 6-methyl-2-aminobenzothiazole. Specifications 345,735 and 347,141 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB732933A GB414452A (en) | 1933-03-10 | 1933-03-10 | The manufacture of asymmetrical thiourea-derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB732933A GB414452A (en) | 1933-03-10 | 1933-03-10 | The manufacture of asymmetrical thiourea-derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB414452A true GB414452A (en) | 1934-08-09 |
Family
ID=9831016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB732933A Expired GB414452A (en) | 1933-03-10 | 1933-03-10 | The manufacture of asymmetrical thiourea-derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB414452A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367345A (en) * | 1980-05-06 | 1983-01-04 | Ihara Chemical Industry Co., Ltd. | Process for producing tolylthiourea having high purity |
-
1933
- 1933-03-10 GB GB732933A patent/GB414452A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367345A (en) * | 1980-05-06 | 1983-01-04 | Ihara Chemical Industry Co., Ltd. | Process for producing tolylthiourea having high purity |
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