Sodium Carbonate → 4-Thiazolecarboxylic acid, 5-phenyl-2-(trifluoromethyl)-, ethyl ester

HRID 383927

반응식

HRID 383927 반응식
Cl[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[S:19].C([O-])([O-])=O.[Na+].[Na+]>CC#N>[C:10]1([C:2]2[S:19][C:18]([C:17]([F:22])([F:21])[F:16])=[N:20][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 4425751TrifluoroethanethioamideHCID 13833360Ethyl 3-chloro-2-oxo-3-phenylpropanoate

생성물 1

HCID 592913484-Thiazolecarboxylic acid, 5-phenyl-2-(trifluoromethyl)-, ethyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of ethyl 3-chloro-2-oxo-3-phenylpropanoate and trifluorothioacetamide in MeCN was heated under reflux. To the reaction mixture was added an aqueous Na2CO3 solution, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain ethyl 5-phenyl-2-(trifluoromethyl)-1,3-thiazole-4-carboxylate as a white solid.

후처리

  1. temperatureunder reflux
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with water and brine in this order
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc)

출처 및 근거

ORD 기록
ord-4aba71c0bc784a9fb07d98cc7ee5226f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367696B2

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