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

HRID 1172867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172867
[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
  4. customchromatography (2:8; EtOAc:hexanes) to give a pale-white solid

Quellen und Nachweise

ORD-Eintrag
ord-290e452bee0743e7bf3dde8778db69ae
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834034B2

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