2,6-Dichlorobenzamide → 2,6-Dichlorobenzoyl isocyanate

HRID 46469Notes

Reaction equation

HRID 46469 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:13](Cl)=[O:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([N:6]=[C:13]=[O:14])=[O:5]

Participants

4

Reactant 2

HCID 161832,6-DichlorobenzamideHCID 65578Oxalyl chloride

Product 1

HCID 129127392,6-Dichlorobenzoyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A one-liter flask was purged with nitrogen while dry 2,6-dichlorobenzamide (125 grams, 0.64 mole) and dry toluene (300 ml.) were added. The nitrogen purge was continued as oxalyl chloride (100 grams, 0.79 mole) was added over a 15-minute period, with stirring. The reaction mixture was then heated to 55° C. and stirred overnight (about 18 hours) at 55° C.

Workup

  1. additionwere added
  2. customThe nitrogen purge
  3. additionwas added over a 15-minute period
  4. stirringstirred overnight (about 18 hours) at 55° C.

Sources & evidence

ORD record
ord-e542a430d3694ba49054ec446890242b
Source dataset
uspto-grants-1979_11
Patent number
US04173639

Reaction notes

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