Triethylamine → 4-[4-(2-Chloro-phenoxy)-butyrylamino]-thiophene-3-carboxylic acid methyl ester

HRID 14600

反応式

HRID 14600 の反応式
Cl.[CH3:2][O:3][C:4]([C:6]1[C:10]([NH2:11])=[CH:9][S:8][CH:7]=1)=[O:5].C(N(CC)CC)C.[Cl:19][C:20]1[CH:32]=[CH:31][CH:30]=[CH:29][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>ClCCl>[CH3:2][O:3][C:4]([C:6]1[C:10]([NH:11][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][O:22][C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[Cl:19])=[CH:9][S:8][CH:7]=1)=[O:5]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2777609Methyl 4-aminothiophene-3-carboxylate HydrochlorideHCID 137214424-(2-Chloro-phenoxy)-butyryl chloride

生成物 1

HCID 686879784-[4-(2-Chloro-phenoxy)-butyrylamino]-thiophene-3-carboxylic acid methyl ester収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To 4-amino-thiophene-3-carboxylic acid methyl ester hydrochloride (199 mg, 0.994 mmol) in dichloromethane (1.9 mL) and triethylamine (0.29 mL, 2.08 mmol), was slowly added a crude solution of 4-(2-chloro-phenoxy)-butyryl chloride (271 mg, approximately 1.16 mmol) in dichloromethane (1.9 mL). The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was then further diluted with dichloromethane (50 mL) and washed with water. The aqueous phase was then extracted with dichloromethane and the combined organic phases were dried with sodium sulfate, and concentrated in vacuo. The residue was then purified by column chromatography (SiO2, Heptane/EtOAc: 0-80%) to yield the title compound as a white solid (281 mg, 80%).

後処理

  1. washwashed with water
  2. extractionThe aqueous phase was then extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by column chromatography (SiO2, Heptane/EtOAc: 0-80%)

出典と根拠

ORDレコード
ord-3cab4796b04140f4a3017521a6e9df0b
出典データセット
uspto-grants-2010_06
特許番号
US07732452B2

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