Methoxyacetyl chloride → N-(3-Ethynylphenyl)-2-methoxyacetamide

HRID 271119Notes

Reaction equation

HRID 271119 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH3:10][O:11][CH2:12][C:13](Cl)=[O:14]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:13](=[O:14])[CH2:12][O:11][CH3:10])[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 40141951N-(3-Ethynylphenyl)-2-methoxyacetamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 3-ethynylphenylamine (7.02 g, 60 mmol) in methylene chloride is added a solution of methoxyacetyl chloride (7.8 g, 72 mmol) in methylene chloride (10 mL) dropwise over a period of 30 min at 0° C. After addition, the reaction mixture is allowed to warm-up to room temperature and stirred overnight. The solvent is evaporated and the residue is partitioned between water and ethyl acetate. The organic phase is washed with saturated NaHCO3, H2O, dried (MgSO4) and concentrated to afford the title compound as a colorless oil 10.2 g (90%). 1HNMR (CDCl3): δ (ppm) 3.04 (s, 1H,), 3.48 (s, 3H), 3.98 (s, 2H), 7.24 (m, 2H), 7.61 (d, 1H), 7.66 (s, 1H), 8.21 (s, b, 1H).

Workup

  1. additionAfter addition
  2. customThe solvent is evaporated
  3. customthe residue is partitioned between water and ethyl acetate
  4. washThe organic phase is washed with saturated NaHCO3, H2O
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a9473f7783fa4c52b813af70d798d54f
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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