DE1445581A1 - N-[5-Methyloxazolinyl-(2)]-N'-aryl-Harnstoffderivate und Verfahren zu deren Herstellung - Google Patents
N-[5-Methyloxazolinyl-(2)]-N'-aryl-Harnstoffderivate und Verfahren zu deren HerstellungInfo
- Publication number
- DE1445581A1 DE1445581A1 DE19631445581 DE1445581A DE1445581A1 DE 1445581 A1 DE1445581 A1 DE 1445581A1 DE 19631445581 DE19631445581 DE 19631445581 DE 1445581 A DE1445581 A DE 1445581A DE 1445581 A1 DE1445581 A1 DE 1445581A1
- Authority
- DE
- Germany
- Prior art keywords
- derivatives
- oxazolidine
- imino
- preparation
- phenyl
- 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 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- ILLXLIKVXGHEOL-UHFFFAOYSA-N 5-(chloromethyl)-4,5-dihydro-1,3-oxazol-2-amine Chemical compound NC1=NCC(CCl)O1 ILLXLIKVXGHEOL-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- ZHFKVNRMZIOKGZ-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1,3-oxazol-2-amine Chemical compound CC1CNC(=N)O1 ZHFKVNRMZIOKGZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- -1 phenyl isocyanate isocyanates Chemical class 0.000 claims description 2
- HBVZPVWFLGXUAU-UHFFFAOYSA-N 5-methyl-1,3-oxazolidine Chemical class CC1CNCO1 HBVZPVWFLGXUAU-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000001773 anti-convulsant effect Effects 0.000 description 6
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- NQJMAAZEBNLAJX-UHFFFAOYSA-N 5-(chloromethyl)-1,3-oxazolidine Chemical class ClCC1CNCO1 NQJMAAZEBNLAJX-UHFFFAOYSA-N 0.000 description 1
- 101150038108 Art7 gene Proteins 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0022520 | 1960-10-13 | ||
| DEC0022771 | 1960-11-19 | ||
| DEC0029096 | 1963-02-06 | ||
| DEC0029097 | 1963-02-06 | ||
| DEC29099A DE1247318B (de) | 1960-10-13 | 1963-02-06 | Verfahren zur Herstellung von N-[5-Chlormethyloxazolinyl-(2)]-thioharnstoffderivaten |
| GB2988/64A GB1023386A (en) | 1960-10-13 | 1964-01-23 | Derivatives of 5-methyl-oxazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445581A1 true DE1445581A1 (de) | 1969-06-04 |
Family
ID=27544784
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC29099A Pending DE1247318B (de) | 1960-10-13 | 1963-02-06 | Verfahren zur Herstellung von N-[5-Chlormethyloxazolinyl-(2)]-thioharnstoffderivaten |
| DE19631445581 Pending DE1445581A1 (de) | 1960-10-13 | 1963-02-06 | N-[5-Methyloxazolinyl-(2)]-N'-aryl-Harnstoffderivate und Verfahren zu deren Herstellung |
| DE19631445582 Pending DE1445582A1 (de) | 1960-10-13 | 1963-02-06 | Verfahren zur Herstellung von Derivaten des 5-Chlormethyl-oxazolidins |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC29099A Pending DE1247318B (de) | 1960-10-13 | 1963-02-06 | Verfahren zur Herstellung von N-[5-Chlormethyloxazolinyl-(2)]-thioharnstoffderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631445582 Pending DE1445582A1 (de) | 1960-10-13 | 1963-02-06 | Verfahren zur Herstellung von Derivaten des 5-Chlormethyl-oxazolidins |
Country Status (5)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5263779A (en) * | 1978-11-29 | 1980-05-29 | Beecham Group Limited | Derivatives of thiazolidin-2-ylidene and oxazolidin-2-ylidene with hypoglycaemic acitivity |
| PT77429B (fr) * | 1982-10-05 | 1986-02-27 | Cortial | Procede pour preparer de nouvelles n-(amino-methyl-5 oxazolin-2 yl-2)n'-phenylurees et de compositions les contenant |
| PT77428B (fr) * | 1982-10-05 | 1986-02-27 | Cortial | Procede pour preparer de nouvelles amino-2-substitue-5-oxazoli-nes-2 et des compositions les contenant |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2661272A (en) * | 1950-09-21 | 1953-12-01 | Du Pont | 1-cyclohexyl-3, 3-dialkylureas and their use as herbicides |
| NL280954A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-07-14 |
-
1963
- 1963-02-06 DE DEC29099A patent/DE1247318B/de active Pending
- 1963-02-06 DE DE19631445581 patent/DE1445581A1/de active Pending
- 1963-02-06 DE DE19631445582 patent/DE1445582A1/de active Pending
- 1963-12-23 CH CH1588063A patent/CH483438A/de not_active IP Right Cessation
-
1964
- 1964-01-23 GB GB2988/64A patent/GB1023386A/en not_active Expired
- 1964-02-03 BE BE643289D patent/BE643289A/xx unknown
- 1964-02-05 US US347067A patent/US3299089A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE643289A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-08-03 |
| DE1247318B (de) | 1967-08-17 |
| GB1023386A (en) | 1966-03-23 |
| CH483438A (de) | 1969-12-31 |
| US3299089A (en) | 1967-01-17 |
| DE1445582A1 (de) | 1969-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |