Ethyl bromopyruvate → 3-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester

HRID 416615

反応式

HRID 416615 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)([O-:3])=[O:2].Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(C(C)=O)C>[CH2:22]([O:21][C:19]([C:18]1[N:15]=[C:12]2[N:11]([CH:17]=1)[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[CH:14][S:13]2)=[O:20])[CH3:23]

参加物

4

反応物 2

HCID 66144Ethyl bromopyruvate2 回HCID 5957794-(2-Nitrophenyl)thiazole-2-amine

生成物 1

HCID 596802093-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester収率 52.5%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

4-(2-Nitro-phenyl)-thiazol-2-ylamine (1.60 g, 7.2 mmol) was mixed with 50 mL of methyl ethyl ketone along 0.90 mL of ethyl bromopyruvate (7.2 mmol) and stirred under reflux for 24 hours. Another equivalent of ethyl bromopyruvate (0.90 mL, 7.2 mmol) was added and the reaction mixture was stirred under reflux for another 8 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 5% MeOH) to afford 1.2 g of 3-(2-nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester (52% yield).

後処理

  1. temperatureunder reflux for 24 hours
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for another 8 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 5% MeOH)

出典と根拠

ORDレコード
ord-7815c6ec702742418905e96115fc4fe0
出典データセット
uspto-grants-2012_01
特許番号
US08088928B2

関連ノート

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