Ethanol → 2-(Pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

HRID 460164

반응식

HRID 460164 반응식
[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[S:3].Br[CH2:11][C:12](=O)[C:13]([O:15]CC)=[O:14].CCO.O[Li].O>CO>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:2]1[S:3][CH:11]=[C:12]([C:13]([OH:15])=[O:14])[N:1]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 168937Lithium hydroxide, monohydrateHCID 1549499Pyridine-2-carbothioamide

생성물 1

HCID 156230902-(Pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Amino-2-pyridylmethane-1-thione (1.88 g, 0.0136 mol), ethyl bromopyruvate (1.80 mL, 0.0143 mol) and EtOH (30 mL) were combined and heated to reflux. GC/MS of reaction mixture after 3 h showed total consumption of the starting materials. After cooling to RT, the solvent was removed under vacuum resulting in a dark brown oil (GC/MS m/z: 235 (M+H); GC Retention time: 10.69 min). The material was taken up in MeOH (20 mL), 1.0M LiOH—H2O (20 mL) was added and the mixture was heated to 100° C. for 14 h. After cooling to RT, the excess MeOH was evaporated and the resulting brown solid filtered. The material was washed with a minimum of H2O and dried in vacuo to give the thiazole as a brown solid.

후처리

  1. temperatureheated to reflux
  2. customGC/MS of reaction mixture after 3 h
  3. customconsumption of the starting materials
  4. customthe solvent was removed under vacuum
  5. customresulting in a dark brown oil (GC/MS m/z: 235 (M+H); GC Retention time: 10.69 min)
  6. temperaturethe mixture was heated to 100° C. for 14 h
  7. temperatureAfter cooling to RT
  8. customthe excess MeOH was evaporated
  9. filtrationthe resulting brown solid filtered
  10. washThe material was washed with a minimum of H2O
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-b92bd35fb3b8483dbe0338fae21b0283
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196104B2

연결된 노트

불러오는 중…