DE1618106A1 - Verfahren zur Herstellung von N,N'-disubstituierten Thioharnstoffen - Google Patents
Verfahren zur Herstellung von N,N'-disubstituierten ThioharnstoffenInfo
- Publication number
- DE1618106A1 DE1618106A1 DE19671618106 DE1618106A DE1618106A1 DE 1618106 A1 DE1618106 A1 DE 1618106A1 DE 19671618106 DE19671618106 DE 19671618106 DE 1618106 A DE1618106 A DE 1618106A DE 1618106 A1 DE1618106 A1 DE 1618106A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- preparation
- thioureas
- mixture
- disubstituted
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000003585 thioureas Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 methylene halides Chemical class 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical group NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- HAAZMOAXEMIBAJ-UHFFFAOYSA-N 4-chloro-2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC(Cl)=C21 HAAZMOAXEMIBAJ-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0091511 | 1967-03-08 | ||
| DEB0091657 | 1967-03-17 | ||
| DEB0091726 | 1967-03-22 | ||
| DEB0093320 | 1967-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618106A1 true DE1618106A1 (de) | 1971-05-13 |
Family
ID=27436674
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618106 Pending DE1618106A1 (de) | 1967-03-08 | 1967-03-08 | Verfahren zur Herstellung von N,N'-disubstituierten Thioharnstoffen |
| DE19671618121 Pending DE1618121A1 (de) | 1967-03-08 | 1967-03-22 | Verfahren zur Herstellung von N,N'-disubstituierten Thioharnstoffen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618121 Pending DE1618121A1 (de) | 1967-03-08 | 1967-03-22 | Verfahren zur Herstellung von N,N'-disubstituierten Thioharnstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE711626A (enrdf_load_stackoverflow) |
| CH (1) | CH484081A (enrdf_load_stackoverflow) |
| DE (2) | DE1618106A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1554529A (enrdf_load_stackoverflow) |
| GB (1) | GB1219851A (enrdf_load_stackoverflow) |
| NL (1) | NL6803268A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349674B (zh) * | 2022-01-17 | 2023-05-05 | 华南理工大学 | 一种硫脲类化合物及其制备方法 |
-
1967
- 1967-03-08 DE DE19671618106 patent/DE1618106A1/de active Pending
- 1967-03-22 DE DE19671618121 patent/DE1618121A1/de active Pending
-
1968
- 1968-02-23 CH CH261968A patent/CH484081A/de not_active IP Right Cessation
- 1968-02-27 FR FR1554529D patent/FR1554529A/fr not_active Expired
- 1968-03-04 BE BE711626D patent/BE711626A/xx unknown
- 1968-03-07 GB GB1107068A patent/GB1219851A/en not_active Expired
- 1968-03-07 NL NL6803268A patent/NL6803268A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6803268A (enrdf_load_stackoverflow) | 1968-09-09 |
| GB1219851A (en) | 1971-01-20 |
| CH484081A (de) | 1970-01-15 |
| DE1618121A1 (de) | 1971-12-09 |
| FR1554529A (enrdf_load_stackoverflow) | 1969-01-17 |
| BE711626A (enrdf_load_stackoverflow) | 1968-09-04 |
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