Methylamine → 3-Cyano-N-methylbenzamide

HRID 1830874Notes

Reaction equation

HRID 1830874 reaction equation
[CH3:1][NH2:2].[C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])#[N:4]>C1COCC1>[C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH:2][CH3:1])=[O:9])#[N:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 220496963-Cyano-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 40% aqueous methylamine solution (20 ml) and THF (30 ml) was cooled to 5° C., and 3-cyanobenzoyl chloride (1.89 g) was slowly added. The mixture was stirred for one hr. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried and concentrated. The residue was recrystallized from ethyl acetate to give the title compound (1.14 g) as colorless needle crystals.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f0ba064e98704e17b2865c55a6045f08
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

Loading…