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

HRID 383927

反応式

HRID 383927 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4aba71c0bc784a9fb07d98cc7ee5226f
出典データセット
uspto-grants-2013_02
特許番号
US08367696B2

関連ノート

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