2,6-Difluorobenzoyl isocyanate → HCID 13338277, compound

HRID 358456Notes

Reaction equation

HRID 358456 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:16]=[C:17]([NH2:29])[CH:18]=[C:19]([Cl:28])[C:20]=1[O:21][C:22]([F:27])([F:26])[CH:23]([Cl:25])[F:24]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[C:17]([NH:29][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])=[O:8])[CH:18]=[C:19]([Cl:28])[C:20]=1[O:21][C:22]([F:27])([F:26])[CH:23]([Cl:25])[F:24]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 13503378HCID 13503378, compound

Product 1

HCID 13338277HCID 13338277, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-Difluorobenzoyl isocyanate (5.5 g, 0.03 mole) was added to a solution of 3,5-dichloro-4-(2-chloro-1,1,2-trifluoroethoxy)benzenamine (8.8 g, 0.03 mole) in 150 ml toluene and heated under reflux with stirring for one hour giving a clear solution. Toluene was removed by evaporation in a rotary evaporator. The residue was recrystallized from aqueous acetic acid and then from acetonitrile giving a white solid (8.3 g, 58 percent yield), melting at 178°-180° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customgiving a clear solution
  4. customToluene was removed by evaporation in a rotary evaporator
  5. customThe residue was recrystallized from aqueous acetic acid

Sources & evidence

ORD record
ord-3ad6bdd1428d449ab4a57409ac1a2e22
Source dataset
uspto-grants-1984_08
Patent number
US04468405

Reaction notes

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