Cyclohexyl isocyanate → N-cyclohexyl-N'-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]urea

HRID 9409

Reaction equation

HRID 9409 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]([CH3:19])([NH2:18])[CH3:17])=[CH:11][CH:10]=[C:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:8]=2)([O-:3])=[O:2].[CH:26]1([N:32]=[C:33]=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>ClCCl>[CH:26]1([NH:32][C:33]([NH:18][C:16]([CH3:19])([CH3:17])[CH2:15][NH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:10][CH:11]=3)[N:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 86593761N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine

Product 1

HCID 21984292N-cyclohexyl-N'-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine (3.56 g, 10.6 mmol) in dichloromethane (100 mL) was cooled to 0° C. Cyclohexyl isocyanate (3.00 mL, 23.5 mmol) was added over the course of a day, and the reaction was stirred at ambient temperature for three days. The solvent was removed under reduced pressure. Xylenes (3 cx 100 mL) were added and removed under reduced pressure to provide N-cyclohexyl-N′-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]urea as a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionXylenes (3 cx 100 mL) were added
  3. customremoved under reduced pressure

Sources & evidence

ORD record
ord-9d81f920428647a890f47a570c783a86
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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