DE2202369A1 - Verfahren zur herstellung von thiazolinen-(2) - Google Patents
Verfahren zur herstellung von thiazolinen-(2)Info
- Publication number
- DE2202369A1 DE2202369A1 DE19722202369 DE2202369A DE2202369A1 DE 2202369 A1 DE2202369 A1 DE 2202369A1 DE 19722202369 DE19722202369 DE 19722202369 DE 2202369 A DE2202369 A DE 2202369A DE 2202369 A1 DE2202369 A1 DE 2202369A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- radical
- dithiocarboxylic
- thiazoline
- 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 7
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001541 aziridines Chemical class 0.000 claims description 4
- 150000002023 dithiocarboxylic acids Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 11
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 8
- -1 heterocyclic radical Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZGRWZUDBZZBJQB-UHFFFAOYSA-N benzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC=C1 ZGRWZUDBZZBJQB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003549 thiazolines Chemical class 0.000 description 3
- VJMKUIGXCSGCIB-UHFFFAOYSA-N 2-chlorobenzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC=C1Cl VJMKUIGXCSGCIB-UHFFFAOYSA-N 0.000 description 2
- IEWSAKJQUJUZNZ-UHFFFAOYSA-N 3-chlorobenzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC(Cl)=C1 IEWSAKJQUJUZNZ-UHFFFAOYSA-N 0.000 description 2
- ZYXBMZWOPXQKMJ-UHFFFAOYSA-N 4-chlorobenzenecarbodithioic acid Chemical compound SC(=S)C1=CC=C(Cl)C=C1 ZYXBMZWOPXQKMJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- ZLYGFPYRVOKHNU-UHFFFAOYSA-N FC(C=1C=C(C(=S)S)C=CC=1)(F)F Chemical compound FC(C=1C=C(C(=S)S)C=CC=1)(F)F ZLYGFPYRVOKHNU-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- DNPSMEGHIHDFAJ-UHFFFAOYSA-N 2,3-dimethylaziridine Chemical compound CC1NC1C DNPSMEGHIHDFAJ-UHFFFAOYSA-N 0.000 description 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
- LKQAJXTWYDNYHK-UHFFFAOYSA-N 2-benzylaziridine Chemical compound C=1C=CC=CC=1CC1CN1 LKQAJXTWYDNYHK-UHFFFAOYSA-N 0.000 description 1
- HRLVJFPTQYDJKX-UHFFFAOYSA-N 2-bromobenzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC=C1Br HRLVJFPTQYDJKX-UHFFFAOYSA-N 0.000 description 1
- YQVZLVXTBKNYNY-UHFFFAOYSA-N 2-cyclohexylaziridine Chemical compound C1NC1C1CCCCC1 YQVZLVXTBKNYNY-UHFFFAOYSA-N 0.000 description 1
- VGNRGNPPDGXIEN-UHFFFAOYSA-N 2-cyclopentylaziridine Chemical compound C1NC1C1CCCC1 VGNRGNPPDGXIEN-UHFFFAOYSA-N 0.000 description 1
- AKDBYIZWQOHKDB-UHFFFAOYSA-N 2-ethylbenzenecarbodithioic acid Chemical compound CCC1=CC=CC=C1C(S)=S AKDBYIZWQOHKDB-UHFFFAOYSA-N 0.000 description 1
- NKGPSOBDVMBRSX-UHFFFAOYSA-N 2-hexylaziridine Chemical compound CCCCCCC1CN1 NKGPSOBDVMBRSX-UHFFFAOYSA-N 0.000 description 1
- VDVCHDOKGYJHMZ-UHFFFAOYSA-N 2-methyl-3-propylaziridine Chemical compound CCCC1NC1C VDVCHDOKGYJHMZ-UHFFFAOYSA-N 0.000 description 1
- HSUQLHINGGUCOA-UHFFFAOYSA-N 4-butoxybenzenecarbodithioic acid Chemical compound CCCCOc1ccc(cc1)C(S)=S HSUQLHINGGUCOA-UHFFFAOYSA-N 0.000 description 1
- NMHGKQRBLJOZEL-UHFFFAOYSA-N 4-methylbenzenecarbodithioic acid Chemical compound CC1=CC=C(C(S)=S)C=C1 NMHGKQRBLJOZEL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722202369 DE2202369A1 (de) | 1972-01-19 | 1972-01-19 | Verfahren zur herstellung von thiazolinen-(2) |
| CH56573A CH568999A5 (cg-RX-API-DMAC7.html) | 1972-01-19 | 1973-01-16 | |
| FR7302005A FR2168579A1 (en) | 1972-01-19 | 1973-01-19 | 2-substd 2-thiazolines prepn - by reacting dithiocarboxylic acids with ethylenimines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722202369 DE2202369A1 (de) | 1972-01-19 | 1972-01-19 | Verfahren zur herstellung von thiazolinen-(2) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2202369A1 true DE2202369A1 (de) | 1973-07-26 |
Family
ID=5833387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722202369 Pending DE2202369A1 (de) | 1972-01-19 | 1972-01-19 | Verfahren zur herstellung von thiazolinen-(2) |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH568999A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2202369A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2168579A1 (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4336387A (en) * | 1981-03-02 | 1982-06-22 | Polaroid Corporation | Thiazolidine-substituted phenyl sulfonyl chlorides |
-
1972
- 1972-01-19 DE DE19722202369 patent/DE2202369A1/de active Pending
-
1973
- 1973-01-16 CH CH56573A patent/CH568999A5/xx not_active IP Right Cessation
- 1973-01-19 FR FR7302005A patent/FR2168579A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4336387A (en) * | 1981-03-02 | 1982-06-22 | Polaroid Corporation | Thiazolidine-substituted phenyl sulfonyl chlorides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2168579B1 (cg-RX-API-DMAC7.html) | 1982-03-26 |
| FR2168579A1 (en) | 1973-08-31 |
| CH568999A5 (cg-RX-API-DMAC7.html) | 1975-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |