Triethylamine → Rac-4-(2-chloro-propionylamino)-thiophene-3-carboxylic acid methyl ester

HRID 14611

反応式

HRID 14611 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][S:7][CH:6]=1)=[O:4].[Cl:11][CH:12]([CH3:16])[C:13](Cl)=[O:14].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:13](=[O:14])[CH:12]([Cl:11])[CH3:16])=[CH:8][S:7][CH:6]=1)=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 2777610Methyl 4-aminothiophene-3-carboxylate

生成物 1

HCID 68688356Rac-4-(2-chloro-propionylamino)-thiophene-3-carboxylic acid methyl ester収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-15 °C

実験手順

To a suspension of 4-amino-thiophene-3-carboxylic acid methyl ester (2.0g) in dichloromethane (25 mL) was added 2-chloropropionyl chloride (1.13 mL). The reaction mixture was then cooled down to −15° C. and a solution of triethylamine (3.2 mL) in dichloromethane (5 mL) was slowly added over 30 minutes. After such time the reaction mixture was allowed to warm up to room temperature, and the solution was washed twice with water, dried over sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a light yellow solid (2.1g, 82%). MS (EI): 247.0.

後処理

  1. temperatureto warm up to room temperature
  2. washthe solution was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-b604834c7358483795593421fbc68b98
出典データセット
uspto-grants-2010_06
特許番号
US07732452B2

関連ノート

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