Acetic acid, 2,2-dimethoxy-, methyl ester → N-(2-bromobenzyl)-2,2-dimethoxyacetamide

HRID 1926275Notes

Reaction equation

HRID 1926275 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14]>>[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH:14][C:4](=[O:5])[CH:3]([O:8][CH3:9])[O:2][CH3:1]

Participants

3

Reactant 2

HCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 3340722-Bromobenzylamine

Product 1

HCID 67520920N-(2-bromobenzyl)-2,2-dimethoxyacetamide

Conditions

Temperature
50 °C

Procedure

Into a sealed tube were added methyl dimethoxyacetate (1.0 g, 7.5 mmol) and 2-bromobenzylamine (1.1 g, 5.8 mmol), this mixture was stirred at 50° C. for 16 h. The completed reaction was transferred to a flask and re-crystallized from heptane yielding the desired product as an off-white solid. MS (ES+): m/z=288.04/289.69 [MH+]. HPLC: tR=2.93 min (ZQ3, polar—5 min).

Workup

  1. customThe completed reaction
  2. customwas transferred to a flask
  3. customre-crystallized from heptane yielding the desired product as an off-white solid
  4. custom5 min

Sources & evidence

ORD record
ord-33ce4ae911574c06ab81c6069c1c6ab0
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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