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

HRID 1818159Notes

Reaction equation

HRID 1818159 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-81291b5fc39b44ac870352503900a85f
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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