Water → 3-(Benzyloxy)-N-methoxy-N-methylbenzamide

HRID 856966Notes

Reaction equation

HRID 856966 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)CC)C.O>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([N:20]([O:21][CH3:22])[CH3:19])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3092263-(Benzyloxy)benzoic acid

Product 1

HCID 218653613-(Benzyloxy)-N-methoxy-N-methylbenzamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 136.8 g (0.60 mol) 3-benzyloxybenzoic acid in 1200 ml dichloromethane 60.6 g (0.6 mol) triethylamine was added at 10° C. A solution of 64.8 g (0.60 mol) ethyl chloroformiate in 100 ml dichloromethane was added over a period of 15 minutes keeping the temperature between 10° C. and 15° C. After stirring for 40 minutes and addition of 58.2 g (0.60 mol) N,O-dimethylhydroxylamine hydrochloride a solution of 60.6 g (0.60 mol) triethylamine was added over a period of 20 minutes at 10–15° C. After additional strirring for 30 minutes water was added and the organic layer dried over sodium sulphate. Fractionated distillation in vacuo yielded 131.9 g (81%) B1.

Workup

  1. additionwas added at 10° C
  2. customthe temperature between 10° C. and 15° C
  3. additionwas added over a period of 20 minutes at 10–15° C
  4. dry with materialthe organic layer dried over sodium sulphate
  5. distillationFractionated distillation in vacuo

Sources & evidence

ORD record
ord-0162025beb9445d7836cd91489cb4682
Source dataset
uspto-grants-2006_12
Patent number
US07144889B2

Reaction notes

Loading…