1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 58024281, compound

HRID 552405Notes

Reaction equation

HRID 552405 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[C:7]=1[N+:13]([O-:15])=[O:14].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34]>>[NH2:12][C:8]1[C:7]([N+:13]([O-:15])=[O:14])=[C:6]([O:5][C:4]2[CH:3]=[C:2]([NH:1][C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[C:25]([C:33]([F:35])([F:34])[F:36])[CH:26]=3)=[O:32])[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=2)[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 58024385HCID 58024385, compound

Product 1

HCID 58024281HCID 58024281, compoundYield 98%

Procedure

Method G was used with 4-(3-amino-5-(trifluoromethyl)phenoxy)-3-nitropyridin-2-amine and 4-chloro-3-trifluoromethylphenyl isocyanate to afford the title compound as a yellow powder (262 mg, 98%). 1H-NMR (δ, ppm, DMSO-d6): 6.17 (d, 1H, HPy,4, J=5.6 Hz), 7.19 (m, 1H, Harom), 7.28 (bs, 2H, NHPy), 7.56 (s, 1H, Harom), 7.61 (d, 1H, Harom, J=8.7 Hz), 7.68 (dd, 1H, Harom, J=8.7 Hz, J=2.1 Hz), 7.80 (s, 1H, Harom), 8.07 (d, 1H, Harom, J=2.3 Hz), 8.08 (d, 1H, HPy,5, J=5.6 Hz), 9.43 (bs, 2H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 101.5 (C-4); 109.9 (C-11); 111.6 (C-9); 113.0 (C-7); 117.1 (C-15); 117.2 (C-2); 122.2 (C-17); 122.8 (C-16); 123.5 (C-19); 124.4 (C-10); 126.6 (C-20); 131.0 (C-12); 131.9 (C-18); 138.7 (C-14); 142.1 (C-8); 152.2 (C-13); 153.5 (C-5); 153.9 (C-1); 154.4 (C-6); 157.8 (C-3). LC-MS (m/z): 536 (M+H, 100).

Sources & evidence

ORD record
ord-e206980799264c6ea2b88aff93df329d
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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