3,5-Dichlorophenyl isocyanate → N-(3,5-Dichlorophenyl)-2-(4,8-dimethylquinolin-2-yl)hydrazinecarboxamide

HRID 1892273

Reaction equation

HRID 1892273 reaction equation
[NH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[C:6]([CH3:14])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[Cl:15][C:16]1[CH:21]=[C:20]([N:22]=[C:23]=[O:24])[CH:19]=[C:18]([Cl:25])[CH:17]=1>>[Cl:15][C:16]1[CH:21]=[C:20]([NH:22][C:23]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH3:13])[C:10]3[C:5](=[C:6]([CH3:14])[CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[O:24])[CH:19]=[C:18]([Cl:25])[CH:17]=1

Participants

3

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 36843162-Hydrazinyl-4,8-dimethylquinoline

Product 1

HCID 52912061N-(3,5-Dichlorophenyl)-2-(4,8-dimethylquinolin-2-yl)hydrazinecarboxamide

Procedure

A solution of 2-hydrazinyl-4,8-dimethylquinoline (100 mg, 0.53 mmol) and 100 mg (1.0 eq) of 1,3-dichloro-5-isocyanatobenzene was reacted as outlined in Scheme 1 above to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.51 (s, 3 H) 2.55 (s, 3 H) 6.77-6.80 (m, 1 H) 7.09 (t, J=1.76 Hz, 1 H) 7.17 (dd, J=8.20, 7.03 Hz, 1 H) 7.40 (d, J=6.74 Hz, 1 H) 7.65-7.72 (m, 3 H) 8.40 (br. s., 1 H) 8.62 (s, 1 H) 9.25 (br. s., 1 H).

Sources & evidence

ORD record
ord-dc8835d90a7743f391887015b90e7de4
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Linked notes

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