1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 42626043, compound

HRID 1864645Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

Method H3 (in DCM). 4-(4-Aminophenoxy)-3-nitropyridin-2-amine (170 mg, 0.69 mmol) was dissolved in dry DCM (5 mL) and cooled to 0° C. 4-Chloro-3-trifluoromethyl-phenyl isocyanate (153 mg, 0.69 mg) was dissolved in dry DCM (3 mL) and was added dropwise to the cooled solution. The reaction mixture was allowed to warm at room temperature and was stirred for 20 hours under argon. The resulting precipitate was recovered by filtration, washed with more DCM and dried, to afford the title compound (240 mg, 74%). 1H-NMR (δ, ppm, DMSO-d6): 5.98 (d, 1H, HPy,5, J=5.0 Hz), 7.14-7.18 (m, 4H, NH2,Py+Harom,Ph,3+5), 7.57 (d, 2H, Harom,Ph,2+6), 7.64 (broad s, 2H, Harom′), 8.00 (d, 1H, HPy,6), 8.13 (s, 1H, Harom′), 9.00 (s, 1H, NHurea,1), 9.21 (s, 1H, NHurea,3); LC-MS (m/z): 468 (M+H, 100).

Workup

additionwas added dropwise to the cooled solution
temperatureto warm at room temperature
filtrationThe resulting precipitate was recovered by filtration
washwashed with more DCM
customdried

Sources & evidence

ORD record: ord-1daa2050837b491bab91d5e60f12bbdf
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625922B2

Reaction notes

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