2,6-Difluorobenzoyl isocyanate → HCID 13591680, compound

HRID 483136Notes

Reaction equation

HRID 483136 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([CH:9]([C:17]#[N:18])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:6]([Cl:19])=[CH:5][C:3]=1[NH2:4].[F:20][C:21]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:22]=1[C:23]([N:25]=[C:26]=[O:27])=[O:24]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([CH:9]([C:17]#[N:18])[C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[C:6]([Cl:19])=[CH:5][C:3]=1[NH:4][C:26]([NH:25][C:23](=[O:24])[C:22]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:21]=1[F:20])=[O:27]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 13591679HCID 13591679, compound

Product 1

HCID 13591680HCID 13591680, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 100 milliliter round bottom flask equipped with a thermometer, magnetic stirrer and condenser was added 30 milliliters of toluene, 1.2 grams (0.004 moles) of 2,5-dichloro-4-(alpha-cyano-4-fluorobenzyl)aniline prepared in Part B and 1.0 grams (0.005 moles) of 2,6-difluorobenzoyl isocyanate under a nitrogen atmosphere at ambient temperature. The reaction mixture was then heated in an oil bath for a period of 2 hours. After cooling to ambient temperature, the reaction mixture was filtered and dried overnight in a vacuum oven at 50° C. This afforded 1.3 grams of a white solid having a melting point of 216° C.-218° C. Elemental analysis of the white solid indicated the following:

Workup

  1. customInto a 100 milliliter round bottom flask equipped with a thermometer, magnetic stirrer and condenser
  2. temperatureThe reaction mixture was then heated in an oil bath for a period of 2 hours
  3. filtrationthe reaction mixture was filtered
  4. customdried overnight in a vacuum oven at 50° C

Sources & evidence

ORD record
ord-eeb1fef274584121bb8ed710499d1e31
Source dataset
uspto-grants-1986_03
Patent number
US04578402

Reaction notes

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