Dimethylformamide → 2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl chloride

HRID 1510283Notes

Reaction equation

HRID 1510283 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12](O)=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:22])=O.CN(C=O)C>C(Cl)Cl>[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12]([Cl:22])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acid

Product 1

HCID 860328062-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (500 mg, 1.90 mmol) in methylene chloride (15 mL) was added oxalyl chloride (0.34 mL, 3.80 mmol) dropwise at 0° C. This was followed by a drop of DMF. The reaction was warmed to room temperature and stirred at room temperature for 1.5 hr. The mixture was concentrated to dryness to afford 2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl chloride as a light yellow solid which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-2a458fb64ce645b18787a9c7f24ce829
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

Loading…