1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 44185962, compound

HRID 1864650Notes

Reaction equation

HRID 1864650 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])=[C:4]([CH3:19])[C:3]=1[CH3:20].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][C:23]=1[C:31]([F:34])([F:33])[F:32]>>[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:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[C:23]([C:31]([F:33])([F:32])[F:34])[CH:24]=3)=[O:30])=[C:3]([CH3:20])[C:4]=2[CH3:19])[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 44185766HCID 44185766, compound

Product 1

HCID 44185962HCID 44185962, compoundYield 86%

Procedure

Method H3 was used with 4-(4-amino-2,3-dimethylphenoxy)-3-nitropyridin-2-amine and 4-chloro-3-trifluoromethyl-phenyl isocyanate to afford the title compound (625 mg, 86%) as a yellow powder. 1H-NMR (δ, ppm, DMSO-d6): 2.07 (s, 3H, CH3), 2.19 (s, 3H, CH3), 5.77 (d, 1H, HPy,5, J=5.7 Hz), 6.98 (d, 1H, Harom, J=8.7 Hz), 7.14 (s, 2H, NH2,Py), 7.57 (d, 1H, Harom, J=8.7 Hz), 7.62 (m, 1H, Harom), 7.96 (d, 1H, HPy,6, J=5.7 Hz), 8.12 (m, 1H, Harom), 8.21 (s, 1H, NHurea1), 9.38 (s, 1H, NHurea3). LC-MS (m/z): 496 (M+H, 100).

Sources & evidence

ORD record
ord-fb09a45f54cd4d44ae56cea995cc5d60
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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