3-Isocyanatobenzonitrile → 1-(3-(4-Bromophenyl)propyl)-3-(3-cyanophenyl)-1-methylurea

HRID 735550Notes

Reaction equation

HRID 735550 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])=[C:2]=[O:3].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][NH:22][CH3:23])=[CH:15][CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[C:2]([NH:1][C:4]2[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[CH:5]=2)=[O:3])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 27333153-IsocyanatobenzonitrileHCID 283505403-(4-Bromophenyl)-N-methylpropan-1-amine

Product 1

HCID 578426211-(3-(4-Bromophenyl)propyl)-3-(3-cyanophenyl)-1-methylureaYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Isocyanatobenzonitrile (202 mg, 1.4 mmol) was added in one portion to a solution of 22B (320 mg, 1.4 mmol) in methylene chloride (10 mL). After stirring overnight the reaction mixture was concentrated in vacuo and purified by flash chromatography (0 to 100% EtOAc in hexanes) to yield 22C (430 mg, 88%) as a clear oil. MS (ESI) m/z 371.92/373.92 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified by flash chromatography (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bc80ec3dbb094c8c893bcaaad977f63b
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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