Oxalyl chloride → 4-Fluoro-1,3-benzoxazol-2-one-7-carboxylic acid chloride

HRID 2395560Notes

Reaction equation

HRID 2395560 reaction equation
[F:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[F:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[C:5]([C:12]([Cl:18])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 146906864-Fluoro-2-oxo-2,3-dihydro-1,3-benzoxazole-7-carboxylic acid

Product 1

HCID 537571174-Fluoro-1,3-benzoxazol-2-one-7-carboxylic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 4-fluoro-1,3-benzoxazol-2-one-7-carboxylic acid (1.79 g) in dry dichloromethane was treated with oxalyl chloride (0.97 g), followed by N,N-dimethylformamide (3 drops) to initiate the reaction. Stirring was maintained under reflux conditions for 1.5 hours and the mixture evaporated to dryness to give 4-fluoro-1,3-benzoxazol-2-one-7-carboxylic acid chloride, used in the next stage without purification.

Workup

  1. customthe reaction
  2. temperaturewas maintained under reflux conditions for 1.5 hours
  3. customthe mixture evaporated to dryness

Sources & evidence

ORD record
ord-aad537e1d627445ca49652c8d898657a
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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