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

HRID 1926235Notes

Reaction equation

HRID 1926235 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][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14]>CCOC(C)=O>[Cl: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

4

Reactant 2

HCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 666482-Chlorobenzylamine

Product 1

HCID 21419368N-[(2-Chlorophenyl)methyl]-2,2-dimethoxyacetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl dimethoxyacetate (1.41 g, 10.4 mmol) and 2-chlorobenzylamine (1.45 g, 9.73 mmol) in a microwave vial was sealed and heated in the microwave reactor to 130° C. for 30 min and then to 140° C. for 40 min. The reaction solution was dissolved in EtOAc (≈60 mL) and washed with dil. HCl, water, sat. Na2CO3 solution, and brine, and dried over MgSO4. The EtOAc extract was filtered, concentrated, and dried in vacuo overnight, giving the title compound as pale yellow oil. 1H NMR (400 MHz, CDCl3): δ=7.41-7.35 & 7.27-7.22 (AA′BB′, 4H), 6.98 (brs, 1H), 4.74 (s, 1H), 4.58 (d, J=6.0 Hz, 2H), 3.40 (s, 6H). MS(ES+): m/z=266.05/268.01 (41/13) [MNa′], 244.07/246.02 (86/58) [MH+], 212.03/214.02 (56/21) [MH+-MeOH], 180.07/182.05 (63/26) [MH+-2 MeOH]. HPLC: tR=2.87 min (polar—5 min, ZQ3).

Workup

  1. customwas sealed
  2. washwashed with dil. HCl, water, sat. Na2CO3 solution, and brine
  3. dry with materialdried over MgSO4
  4. extractionThe EtOAc extract
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customdried in vacuo overnight

Sources & evidence

ORD record
ord-f21e944f00a546989b4d90244a01889f
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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