Acetic acid, 2,2-dimethoxy-, methyl ester → N-[(3-Chlorophenyl)methyl]-2,2-dimethoxyacetamide

HRID 1926296Notes

Reaction equation

HRID 1926296 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15]>>[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH:15][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 77802Benzenemethanamine, 3-chloro-

Product 1

HCID 67521549N-[(3-Chlorophenyl)methyl]-2,2-dimethoxyacetamide

Procedure

Into a vial were added methyl dimethoxyacetate (1.9 g, 14 mmol) and 3-chlorobenzylamine (2.0 g, 14 mmol), this mixture was stirred at room temperature over two days. The product was triturated with hexane (3×) and re-crystallized from hexane, affording the desired product as oil that solidified over time. 1H NMR (400 MHz, CDCl3): δ=3.43 (s, 6H), 4.47 (d, J=6.1 Hz, 2H), 4.77 (s, 1H), 6.91 (br. s., 1H), 7.15-7.21 (m, 1H), 7.25-7.30 (m, 3H). MS (ES+): m/z=243.93/245.81 [MH+]. HPLC: tR=2.80 min (ZQ2, polar—5 min).

Workup

  1. customThe product was triturated with hexane (3×)
  2. customre-crystallized from hexane

Sources & evidence

ORD record
ord-f045eca5da3843f49cbc25ffacf7711a
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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