1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 44186092, compound

HRID 1864652Notes

Reaction equation

HRID 1864652 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]([F:19])[CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>>[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:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:32])([F:31])[F:33])[CH:23]=3)=[O:29])=[CH:3][C:4]=2[F:19])[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 44186162HCID 44186162, compound

Product 1

HCID 44186092HCID 44186092, compoundYield 42%

Procedure

Method H3 was used with 4-(4-amino-2-fluorophenoxy)-3-nitropyridin-2-amine (0.25 g, 0.946 mmol) and 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.21 g, 0.946 mmol) to afford the title compound (0.19 g, 42%). 1H NMR (250 MHz, 6, ppm, DMSO-d6): 5.98 (dd, 1H, Ja=5.7 Hz, Jb=1.0 Hz), 7.21 (s, 2H), 7.26 (dd, 1H, Ja=9.1 Hz, Jb=2.3 Hz), 7.34 (t, 1H, J=8.8 Hz), 7.60-7.73 (m, 3H), 8.01 (d, 1H, J=5.7 Hz), 8.10 (d, 1H, J=2.1 Hz), 9.19 (s, 1H), 9.27 (s, 1H). m/z 486.1 [(M+H)+ calcd. for C19H12ClF4N5O4 485.1].

Sources & evidence

ORD record
ord-03834561511d4c6fa17d7372f0d2b7b3
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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