4-Bromophenyl isocyanate → 1-(4-Bromo-phenyl)-3-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-urea

HRID 2092520Notes

Reaction equation

HRID 2092520 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>C(Cl)Cl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)=[O:9])=[CH:6][CH:7]=2)=[O:26])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 756094-Bromophenyl isocyanateHCID 231408(4-Aminophenyl)(4-methylpiperazin-1-yl)methanone

Product 1

HCID 675146761-(4-Bromo-phenyl)-3-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-ureaYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-amino-phenyl)-(4-methyl-piperazine-1-yl)-methanone (10.0 g, 0.0456 mol) and TEA (4.7 g, 0.0456 mol) in DCM (150 mL) was added 4-bromophenyl isocyanate (10.9 g, 0.0547 mol). The reaction mixture was stirred at room temperature for 12 h. The white solid was obtained and was filtered and dried to afford the title compound [15.0 g, 79%]; LC-MS (ESI): Calculated mass: 416.1; Observed mass: 417.1 [M+H]+ (RT: 0.23 min).

Workup

  1. customThe white solid was obtained
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-2bf6074da6ef4199b937f2810a513df8
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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