Phenyl isocyanate → HCID 57974509, compound

HRID 1864646Notes

Reaction equation

HRID 1864646 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.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[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:26]([NH:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:27])=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 42625414HCID 42625414, compound

Product 1

HCID 57974509HCID 57974509, compoundYield 74%

Procedure

Method H3 was used with 4-(4-aminophenoxy)-3-nitropyridin-2-amine (50 mg, 0.2 mol) and phenyl isocyanate (22 μL, 0.2 mmol) to afford the title compound (54 mg, 74%). 1H-NMR (δ, ppm, DMSO-d6): 5.96 (d, 1H, HPy,5, J=5.72 Hz), 6.99 (t, 1H, Harom,Ph′,4), 7.13-7.16 (m, 4H, NH2,Py+Harom,Ph,3+5), 7.30 (t, 2H, Harom,Ph′,3+5, J=7.90 Hz), 7.48 (d, 2H, Harom,Ph′,2+6′J=7.69 Hz), 7.55 (d, 2H, Harom,Ph,2+6, J=8.93 Hz), 8.00 (d, 1H, HPy,6, J=5.78 Hz), 8.69 (s, 1H, NHurea,1), 8.81 (s, 1H, NHurea,3); LC-MS (m/z): 366 (M+H, 100).

Sources & evidence

ORD record
ord-5832985ecf234f28b4d1c9c6073a7407
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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