2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → 1-(4-(2-Amino-3-nitropyridin-4-yloxy)-2-(methylthio)phenyl)-3-(2-fluoro-5-(trifluoromethyl)phenyl)urea

HRID 1035457Notes

Reaction equation

HRID 1035457 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[S:19][CH3:20].[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=1[N:32]=[C:33]=[O:34]>>[NH2:13][C:9]1[C:8]([N+:14]([O-:16])=[O:15])=[C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([NH:1][C:33]([NH:32][C:23]3[CH:24]=[C:25]([C:28]([F:29])([F:31])[F:30])[CH:26]=[CH:27][C:22]=3[F:21])=[O:34])=[C:3]([S:19][CH3:20])[CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 441860954-(4-Amino-3-(methylthio)phenoxy)-3-nitropyridin-2-amine

Product 1

HCID 469014261-(4-(2-Amino-3-nitropyridin-4-yloxy)-2-(methylthio)phenyl)-3-(2-fluoro-5-(trifluoromethyl)phenyl)ureaYield 37%

Procedure

Using Method F2 with 4-(4-amino-3-(methylthio)phenoxy)-3-nitropyridin-2-amine (1.04 g, 3.57 mmol) and 2-fluoro-5-trifluoromethylphenyl isocyanate, the title compound (664 mg, 37%) was obtained as a yellow powder.

Sources & evidence

ORD record
ord-7d1610e0e6eb40f58c9e94fcbfc03ce2
Source dataset
uspto-grants-2013_10
Patent number
US08546387B2

Reaction notes

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