3-(Trifluoromethyl)phenyl isocyanate → HCID 22632870, compound

HRID 2270227Notes

Reaction equation

HRID 2270227 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C:12]1[C:13](Cl)=[N:14][C:15]([Cl:19])=[C:16]([F:18])[CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>CC(N(C)C)=O>[CH2:1]([O:8][N:9]1[C:10](=[O:11])[C:12]2[CH:17]=[C:16]([F:18])[C:15]([Cl:19])=[N:14][C:13]=2[N:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:35])[F:34])[CH:26]=2)[C:32]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 24758Sodium hydrideHCID 22632919HCID 22632919, compound

Product 1

HCID 22632870HCID 22632870, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using the General Method 5, the reaction of N-benzyloxy-2,6-dichloro-5-fluoro-3-pyridinecarboxamide (Example M-2, 2.00 g, 6.34 mmol) and 60% NaH in oil (300 mg, 7.52 mmol) with 3-trifluoromethylphenyl isocyanate (1.31 mL, 9.51 mmol) in DMA afforded 2.04 g of the title compound as a solid, mp 207-208° C.

Sources & evidence

ORD record
ord-b2be947db41742e3872bc63130d7393f
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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