Chloroacetyl chloride → 6-(2-Chloro-acetylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1172867노트

반응식

HRID 1172867 반응식
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].C([O-])([O-])=O.[Na+].[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([NH:14][C:23](=[O:24])[CH2:22][Cl:21])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]

참가 물질

6

반응물 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 15557582Methyl 6-aminobenzo[b]thiophene-2-carboxylate

생성물 1

HCID 595564046-(2-Chloro-acetylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 6-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (1.0 g, 4.83 mmol) and Na2CO3 (2.05 g, 19.3 mmol) in DMF (10 mL) was added chloroacetylchloride (460 μL, 5.79 mmol.). After stirring for 18 h, the mixture was diluted with EtOAc, filtered and concentrated. The residue was purified by column:chromatography (2:8; EtOAc:hexanes) to give a pale-white solid. MS (EI): cal'd (MH+) 284.01, exp (MH+) 284.15. Also retained ˜50.5% of impure fractions.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by column
  4. customchromatography (2:8; EtOAc:hexanes) to give a pale-white solid

출처 및 근거

ORD 기록
ord-290e452bee0743e7bf3dde8778db69ae
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834034B2

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