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

HRID 545465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545465
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f7a728a4165a4683b58e7892b6195e63
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935724B2

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