Dimethylformamide → 2-(3-Methylisoxazol-5-yl)acetyl chloride

HRID 20269

Reaction equation

HRID 20269 reaction equation
CN(C)C=O.[C:6](Cl)(=O)[C:7]([Cl:9])=[O:8].[CH3:12][C:13]1[CH:17]=[C:16](CC(O)=O)[O:15][N:14]=1>ClCCl>[CH3:12][C:13]1[CH:17]=[C:16]([CH2:6][C:7]([Cl:9])=[O:8])[O:15][N:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acid

Product 1

HCID 123668732-(3-Methylisoxazol-5-yl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylformamide (few drops), followed by oxalyl chloride (9.5 mL, 106 mmol) were added dropwise to a cooled (10° C.) solution of (3-methyl-isoxazol-5-yl)-acetic acid (5 g, 35.4 mmol) in dichloromethane (50 mL), and the solution was allowed to warm to room temperature. The reaction was stirred for a further 3 hours, then concentrated under reduced pressure. The residue was azeotroped with toluene to afford the title compound.

Workup

  1. additionwere added dropwise to
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-35d1a0ec58494321a176c65bca0fac57
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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