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

HRID 545465노트

반응식

HRID 545465 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 chromatography (2:8; EtOAc:hexanes)
  4. customto give a pale-white solid

출처 및 근거

ORD 기록
ord-f7a728a4165a4683b58e7892b6195e63
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935724B2

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