Dimethyl Sulfate → N-(alpha-Cyano-3-phenoxybenzyl)-N,N,N-trimethylammonium methylsulfate

HRID 904901Notes

Reaction equation

HRID 904901 reaction equation
[S:1]([O:6]C)([O:4][CH3:5])(=[O:3])=[O:2].[CH3:8][N:9]([CH3:26])[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1)[C:11]#[N:12]>CC(CC)=O>[CH3:5][O:4][S:1]([O-:6])(=[O:3])=[O:2].[C:11]([CH:10]([N+:9]([CH3:5])([CH3:26])[CH3:8])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1)#[N:12]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 13565187alpha-(Dimethylamino)-3-phenoxybenzeneacetonitrile

Product 1

HCID 13565188N-(alpha-Cyano-3-phenoxybenzyl)-N,N,N-trimethylammonium methylsulfateYield 203.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Dimethyl sulfate (2.52 g) was added to a solution of α-(dimethylamino)-3-phenoxybenzeneacetonitrile (5.2 g) in ethyl methyl ketone (40 ml) and the mixture was stirred overnight at ambient temperature. The solvent was removed by distillation under reduced pressure to give the title compound (7.7 g) as a golden oil. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 3.4 (9H, s, N(CH3)3); 3.65 (3H, s, CH3SO4); 6.7 (1H, s, CH); 7.0-7.7 (9H, m, aromatic protons).

Workup

  1. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-392d9d74b82e46f1983ac4eda1fce2d4
Source dataset
uspto-grants-1983_12
Patent number
US04420614

Reaction notes

Loading…