Oxalyl chloride → 4-(Isocyanatocarbonyl)-1,2-phenylene diacetate

HRID 903807Notes

Reaction equation

HRID 903807 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[C:7]([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][C:21](=[O:23])[CH3:22])[C:14]([NH2:16])=[O:15])(=[O:9])[CH3:8]>ClCCCl>[C:7]([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][C:21](=[O:23])[CH3:22])[C:14]([N:16]=[C:2]=[O:3])=[O:15])(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 133641214-Carbamoyl-1,2-phenylene diacetate

Product 1

HCID 133641224-(Isocyanatocarbonyl)-1,2-phenylene diacetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Oxalyl chloride (10.1 g) was added to a solution of 3,4-diacetoxybenzamide (7.5 g) in 1,2-dichloroethane (80 ml) with stirring under cooling. The mixture was gradually heated to a reflux temperature and allowed to react under reflux for 13 hours. After completion of the reaction, the solvent and excess oxalyl chloride was distilled off under reduced pressure to give 3,4-diacetoxybenzoyl isocyanate which was dissolved in anhydrous dichloromethane (40 ml) for the subsequent reaction.

Workup

  1. temperatureunder cooling
  2. temperatureThe mixture was gradually heated to a reflux temperature
  3. customto react
  4. temperatureunder reflux for 13 hours
  5. customAfter completion of the reaction
  6. distillationthe solvent and excess oxalyl chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-79fe756ddbda412cbb81601c36ad29e0
Source dataset
uspto-grants-1980_10
Patent number
US04229348

Reaction notes

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