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

HRID 545465Notes

Reaction equation

HRID 545465 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f7a728a4165a4683b58e7892b6195e63
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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