JPS6051182A - ３−置換チアゾリジンの製造法 - Google Patents
３−置換チアゾリジンの製造法Info
- Publication number
- JPS6051182A JPS6051182A JP15854383A JP15854383A JPS6051182A JP S6051182 A JPS6051182 A JP S6051182A JP 15854383 A JP15854383 A JP 15854383A JP 15854383 A JP15854383 A JP 15854383A JP S6051182 A JPS6051182 A JP S6051182A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- cyanoimino
- thiazolidine
- substituted
- mol
- 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.)
- Granted
Links
- -1 3-substituted thiazolidine Chemical class 0.000 title claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 18
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 150000003512 tertiary amines Chemical class 0.000 abstract description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 abstract 1
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HBYVPSCMALYOLZ-UHFFFAOYSA-N (3-ethyl-1,3-thiazolidin-2-ylidene)cyanamide Chemical compound CCN1CCSC1=NC#N HBYVPSCMALYOLZ-UHFFFAOYSA-N 0.000 description 3
- FOTLMCLIMIZKGL-UHFFFAOYSA-N (3-methyl-1,3-thiazolidin-2-ylidene)cyanamide Chemical compound CN1CCSC1=NC#N FOTLMCLIMIZKGL-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- KJQRGYHUJOFFIM-UHFFFAOYSA-N 3-ethyl-1,3-thiazolidine Chemical compound CCN1CCSC1 KJQRGYHUJOFFIM-UHFFFAOYSA-N 0.000 description 2
- DGYVIUKQSWPZCL-UHFFFAOYSA-N 3-methyl-1,3-thiazolidine Chemical compound CN1CCSC1 DGYVIUKQSWPZCL-UHFFFAOYSA-N 0.000 description 2
- PXAWJFBUXHYSSW-UHFFFAOYSA-N 3-phenyl-1,3-thiazolidine Chemical compound C1SCCN1C1=CC=CC=C1 PXAWJFBUXHYSSW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NXOMVTLTYYYYPC-UHFFFAOYSA-N 2-phenyl-1,3-thiazolidine Chemical compound N1CCSC1C1=CC=CC=C1 NXOMVTLTYYYYPC-UHFFFAOYSA-N 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15854383A JPS6051182A (ja) | 1983-08-30 | 1983-08-30 | ３−置換チアゾリジンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15854383A JPS6051182A (ja) | 1983-08-30 | 1983-08-30 | ３−置換チアゾリジンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6051182A true JPS6051182A (ja) | 1985-03-22 |
| JPH0477748B2 JPH0477748B2 (cs) | 1992-12-09 |
Family
ID=15674000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15854383A Granted JPS6051182A (ja) | 1983-08-30 | 1983-08-30 | ３−置換チアゾリジンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6051182A (cs) |
-
1983
- 1983-08-30 JP JP15854383A patent/JPS6051182A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0477748B2 (cs) | 1992-12-09 |
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