Methylamine → N-methyl benzothiophene-2-carboxamide

HRID 2112671Notes

Reaction equation

HRID 2112671 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. additionAfter the addition the reaction
  2. concentrationthen was concentrated under vacuum
  3. filtrationTrituration with a cold solution of 4:1 H2O/methanol (50 mL), filtration
  4. customdrying under vacuum

Sources & evidence

ORD record
ord-6b0eeb329f4042a1846532ff34ee2ff8
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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