1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 58024321, compound

HRID 552403Notes

Reaction equation

HRID 552403 reaction equation
[NH2:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[C:9]=1[N+:15]([O-:17])=[O:16].[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]>>[NH2:14][C:10]1[C:9]([N+:15]([O-:17])=[O:16])=[C:8]([O:7][C:6]2[C:5]([Cl:19])=[CH:4][C:3]([Cl:20])=[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])[CH:18]=2)[CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 45140340HCID 45140340, compound

Product 1

HCID 58024321HCID 58024321, compoundYield 73%

Procedure

Method G was used with 4-(5-amino-2,4-dichlorophenoxy)-2-amino-3-nitropyridine and 4-chloro-3-trifluoromethylphenyl isocyanate to afford the title compound as a yellow powder (740 mg, 73%). 1H-NMR (δ, ppm, DMSO-d6): 6.01 (d, 1H, HPy,5, J=5.6 Hz), 7.26 (s, 2H, NH2,Py), 7.62 (m, 2H, Harom), 7.90 (s, 1H, Harom), 8.03 (m, 2H, Harom+HPy6), 8.21 (s, 1H, Harom), 8.63 (s, 1H, NHurea), 9.95 (s, 1H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 99.7 (C-4); 114.1 (C-11); 116.8 (C-); 116.9 (C-); 118.7 (C-); 119.7 (C-); 121.1 (C-); 123.1 (C-); 123.2 (C-); 123.8 (C-); 130.5 (C-); 132.2 (C-); 136.2 (C-10 or 13); 138.5 (C-10 or 13); 147.4 (C-6); 151.7 (C-12); 153.4 (C-5); 153.9 (C-1); 157.6 (C-3). LC-MS (m/z): 535 (M+H, 100).

Sources & evidence

ORD record
ord-9c7a0358b6dd4d4580b53ebf99555696
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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