Acetic acid, 2,2-dimethoxy-, methyl ester → N-(2,5-dichlorobenzyl)-2,2-dimethoxyacetamide

HRID 1926255Notes

Reaction equation

HRID 1926255 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[Cl:10][C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:12]=1[CH2:13][NH2:14]>>[Cl:10][C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[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 457600Benzenemethanamine, 2,5-dichloro-

Product 1

HCID 67520605N-(2,5-dichlorobenzyl)-2,2-dimethoxyacetamide

Procedure

A solution of methyl dimethoxyacetate (0.823 g, 6.08 mmol) and 2,5-dichlorobenzylamine (1.0 g, 5.7 mmol) was heated to 90° C. in a sealed tube for 48 h. The crude material was purified by column chromatography on silica gel [eluting with 40% EtOAc in hexanes] to afford the title compound as a clear oil. 1H NMR (400 MHz, CDCl3) δ=3.41 (s, 6H), 4.53 (d, J=6.6 Hz, 2H), 4.75 (s, 1H), 7.19-7.23 (m, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H). MS (ES+): m/z=278/280/282 [MH+]. HPLC: tR=3.03 min (ZQ2, polar—5 min).

Workup

  1. customThe crude material was purified by column chromatography on silica gel [eluting with 40% EtOAc in hexanes]

Sources & evidence

ORD record
ord-5392780e91fd415d9f4dbabfdf3bbfee
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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