Oxalyl chloride → 2,1,3-Benzoxadiazole-5-carbonyl chloride

HRID 1195678Notes

Reaction equation

HRID 1195678 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:2]=12.C(Cl)(=O)C([Cl:16])=O>CN(C)C=O.C(Cl)Cl>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([Cl:16])=[O:12])[CH:8]=[CH:9][C:2]=12

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27354542,1,3-Benzoxadiazole-5-carboxylic acid

Product 1

HCID 27354532,1,3-Benzoxadiazole-5-carbonyl chlorideYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.84 g (5.0 mmoles) benzofurazan-5-carboxylic acid and 1 drop dimethylformamide in 20 ml methylene chloride cooled in an ice-bath was added 0.70 g (5.5 mmoles) oxalyl chloride. The solution was warmed to room temperature, stirred for 3 hours, and the solvent was removed in vacuo. The residual oil was extracted with 3×15 ml warm hexane. The combined extract was evaporated to dryness, the resulting solid was stirred under 2 ml cold hexane, the hexane was decanted, and the solid was dried to give 0.895 g (98%) crude benzofurazan-5-carbonyl chloride.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe residual oil was extracted with 3×15 ml
  3. temperaturewarm hexane
  4. extractionThe combined extract
  5. customwas evaporated to dryness
  6. stirringthe resulting solid was stirred under 2 ml cold hexane
  7. customthe hexane was decanted
  8. customthe solid was dried

Sources & evidence

ORD record
ord-56595ec24f9141bba5615a350b099e1e
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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