2,4-Dichlorobenzylamine → N-(2,4-Dichlorobenzyl)-2,2-dimethoxyacetamide

HRID 1926299Notes

Reaction equation

HRID 1926299 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[Cl:10][C:11]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14]>>[Cl:10][C:11]1[CH:18]=[C:17]([Cl:19])[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 14852,4-DichlorobenzylamineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl ester

Product 1

HCID 67520704N-(2,4-Dichlorobenzyl)-2,2-dimethoxyacetamide

Conditions

Temperature
50 °C

Procedure

Into a sealed tube were added methyl dimethoxyacetate (0.78 g, 5.8 mmol) and 2,4-dichlorobenzylamine (1.0 g, 5.8 mmol). This mixture was stirred at 50° C. for 36 h. The completed reaction mixture was transferred to a flask and re-crystallized from heptane yielding the desired product as an off-white solid. MS (ES+): m/z=278.10/280.09/282.08 [MH+]. HPLC: tR=3.03 min (ZQ2, polar—5 min).

Workup

  1. customThe completed reaction mixture
  2. customwas transferred to a flask
  3. customre-crystallized from heptane yielding the desired product as an off-white solid
  4. customHPLC: tR=3.03 min (ZQ2, polar—5 min)

Sources & evidence

ORD record
ord-da369d2a16db4c8885d00b694b325e13
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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