Methylamine → N-methyl benzothiophene-2-carboxamide

HRID 225892

Reaction equation

HRID 225892 reaction equation
[CH3:1][NH2:2].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]1[C:12](Cl)=[O:13]>C1COCC1>[CH3:1][NH:2][C:12]([C:4]1[S:3][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=1)=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 142384Benzo[b]thiophene-2-carbonyl Chloride

Product 1

HCID 22593821N-methyl benzothiophene-2-carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 2.0 M methylamine in THF (60 mL) and THF (60 mL) was added dropwise at 0° C. a solution of benzothiophene-2-carbonyl chloride (10.8 g, 55 mmole) in THF (50 mL) over 15 minutes. After the addition-the reaction was allowed to warm to RT then was concentrated under vacuum. Trituration with a cold solution of 4:1 H2O/methanol (50 mL), filtration, and drying under vacuum gave the title compound (10.35 g, 98%) as a white solid: MS (ES) m/e 191.9 (M+H)+.

Workup

  1. concentrationthen was concentrated under vacuum
  2. filtrationTrituration with a cold solution of 4:1 H2O/methanol (50 mL), filtration
  3. customdrying under vacuum

Sources & evidence

ORD record
ord-d92fc660c7974823b70b04e139b7aaf8
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Linked notes

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