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

HRID 1926260Notes

Reaction equation

HRID 1926260 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][NH2:5].[CH3:11][O:12][CH:13]([O:18][CH3:19])[C:14](OC)=[O:15]>CCCCCCC>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[CH2:4][NH:5][C:14](=[O:15])[CH:13]([O:18][CH3:19])[O:12][CH3:11]

Participants

4

Reactant 2

HCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 27736165-Chloro-2-fluorobenzylamine

Product 1

HCID 67520816N-(5-chloro-2-fluorobenzyl)-2,2-dimethoxyacetamide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Equimolar amounts of 2-fluoro-5-chlorobenzylamine (10.0 g, 62.5 mmol) and methyl dimethoxyacetate (8.38 g, 62.5 mmol) were heated in a sealed tube at 100° C. for 16 h. After cooling to RT, to the reaction mixture was added n-heptane (40 mL) and cooled at 4° C. overnight. The solid formed was filtered off and dried in vacuo to give the title compound as off-white solid. 1H NMR (CDCl3, 300 MHz): δ=3.40 (s, 6H), 4.52 (d, J=5.8 Hz, 2H), 4.74 (s, 1H), 6.89 (bs, 1H), 7.01 (t, J=8.4 Hz, 1H), 7.20-7.25 (m, 1H), 7.31-7.36 (m, 1H). MS (ES+): m/z 261.90/263.78 [MH+]. HPLC: tR=2.85 min (ZQ2, polar—5 min).

Workup

  1. temperaturecooled at 4° C. overnight
  2. customThe solid formed
  3. filtrationwas filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-260d47ea28644081acefb0a39217f6be
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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