4-(Trifluoromethyl)phenyl isocyanate → HCID 21252795, compound

HRID 848973Notes

Reaction equation

HRID 848973 reaction equation
[CH3:1][CH:2]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[N:5][NH:4][CH2:3]1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C(#N)C>[CH3:1][CH:2]1[O:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]([F:18])([F:16])[F:17])=[CH:12][CH:13]=2)=[N:5][N:4]([C:28]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:26][CH:25]=2)=[O:29])[CH2:3]1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 21252801HCID 21252801, compound

Product 1

HCID 21252795HCID 21252795, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1 g of the 5,6-dihydro-6-methyl-2-(4-trifluoromethoxyphenyl)-4H-1,3,4-oxadiazine prepared above was dissolved in 10 ml of acetonitrile. 1 g of 4-(trifluoromethyl)phenyl isocyanate was added dropwise and then the resulting reaction mixture was refluxed for two hours. Evaporation of the solvent at reduced pressure afforded 1.5 g of 5,6-dihydro-6-methyl-2-(4-trifluoromethoxy-phenyl)-N-(4-trifluoromethylphenyl)-4H-1,3,4-oxadiazine-4-carboxamide as a solid which was washed with a few milliliters of acetonitrile. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for two hours
  3. customEvaporation of the solvent at reduced pressure

Sources & evidence

ORD record
ord-195784e6676d4d92967a9bafe86d6e75
Source dataset
uspto-grants-2000_01
Patent number
US06011034

Reaction notes

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