2,6-Difluorobenzoyl isocyanate → 3-[3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-6-(2,6-difluorophenyl)-3,4-dihydro-2H-1,3,5-oxadiazine-2,4-dione

HRID 2290715Notes

Reaction equation

HRID 2290715 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]([N:29]=[C:30]=[O:31])[CH:18]=[C:19]([Cl:28])[C:20]=1[O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24]>>[Cl:14][C:15]1[CH:16]=[C:17]([N:29]2[C:7](=[O:8])[N:6]=[C:4]([C:3]3[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=3[F:13])[O:5][C:30]2=[O:31])[CH:18]=[C:19]([Cl:28])[C:20]=1[O:21][C:22]([F:26])([F:27])[CH:23]([F:24])[F:25]

Participants

3

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 202301521,3-Dichloro-5-isocyanato-2-(1,1,2,2-tetrafluoroethoxy)benzene

Product 1

HCID 202301533-[3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-6-(2,6-difluorophenyl)-3,4-dihydro-2H-1,3,5-oxadiazine-2,4-dione

Conditions

Temperature
120 °C

Procedure

With the exclusion of moisture, 5.4 g of 2,6-difluorobenzoylisocyanate are added with stirring to 9.1 g of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenylisocyanate. The temperature is maintained at 120° C. for 14 hours, with stirring being continued until the reaction mixture commences to congeal. When the resultant crystalline slurry has cooled to room temperature, it is triturated with hexane and subsequently filtered with suction. The residue is recrystallised from toluene, affording the title compound of the formula ##STR9## as a white powder with a melting point of 170°-172° C. (compound 1.2.1).

Workup

  1. temperatureWhen the resultant crystalline slurry has cooled to room temperature
  2. customit is triturated with hexane
  3. filtrationsubsequently filtered with suction
  4. customThe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-be56388a5d134fb8824adb17312d0b1d
Source dataset
uspto-grants-1986_10
Patent number
US04618608

Reaction notes

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