Ethyl thiooxamate → Ethyl 4-(3-bromobenzyl)-5-methylthiazole-2-carboxylate

HRID 517552

反応式

HRID 517552 の反応式
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH:10]([CH3:21])[C:11](=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1>CN(C=O)C.CCOC(C)=O>[Br:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][C:11]1[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][C:10]=1[CH3:21]

参加物

5

反応物 2

HCID 2733398Ethyl thiooxamateHCID 867114923-Bromo-1-(3-bromophenyl)butan-2-one

生成物 1

HCID 86711493Ethyl 4-(3-bromobenzyl)-5-methylthiazole-2-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of ethyl 2-amino-2-thioxoacetate (50.9 mg, 0.38 mmol) and 3-bromo-1-(3-bromophenyl)butan-2-one (0.38 mmol, crude from previous step) in DMF (2 mL) was stirred at 70° C. for 12 h. The mixture was diluted with EtOAc and washed with H2O. The organic layer was concentrated, and purified by silica gel column chromatography(0-50% EtOAc/Hexane) to yield a yellowish solid (71 mg, 55% over 2 steps). MS (ES+) C14H14BrNO2S requires: 339, 341 found: 340, 342 [M+H]+(1:1).

後処理

  1. washwashed with H2O
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel column chromatography(0-50% EtOAc/Hexane)
  4. customto yield a yellowish solid (71 mg, 55% over 2 steps)

出典と根拠

ORDレコード
ord-5e08d89a8e144122b3b56f9f5521f41a
出典データセット
uspto-grants-2015_08
特許番号
US09115120B2

関連ノート

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