Water → N-cyanomethyl-N-methyl-2-phenoxybenzamide

HRID 1706599Notes

Reaction equation

HRID 1706599 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]#[N:6].[OH-].[Na+].O.[O:10]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[C:5]([CH2:4][N:3]([CH3:2])[C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 117641Acetonitrile, 2-(methylamino)-, hydrochloride (1:1)HCID 110753032-Phenoxybenzoyl chloride

Product 1

HCID 20333639N-cyanomethyl-N-methyl-2-phenoxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.7 parts of methylaminoacetonitrile hydrochloride was added to a solution of 2 parts of sodium hydroxide in 25 parts of water at ~15°. When the addition was complete a solution of 5.8 parts of 2-phenoxybenzoyl chloride in 50 parts of methylene chloride was added dropwise. The mixture was stirred vigorously for 5 hrs. at ~20°. The methylene chloride layer was then separated, washed with water and dried over magnesium sulfate. Removal of the magnesium sulfate by filtration and concentration of the filtrate gave 4.6 parts of N-cyanomethyl-N-methyl-2-phenoxybenzamide as a viscous oil. NMR (CDCl3) 3δ(S,3H,CH3), 4.1δ,4.3δ (2S,2H,CH2), 7.05δ, (m,9H,Aromatic H).

Workup

  1. additionWhen the addition
  2. additionwas added dropwise
  3. customat ~20°
  4. customThe methylene chloride layer was then separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the magnesium sulfate
  8. filtrationby filtration and concentration of the filtrate

Sources & evidence

ORD record
ord-8dd951a654b440ec948e08775ce8016d
Source dataset
uspto-grants-1980_06
Patent number
US04208205

Reaction notes

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