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

HRID 14600

반응식

HRID 14600 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-3cab4796b04140f4a3017521a6e9df0b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732452B2

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