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

HRID 517423Notes

Reaction equation

HRID 517423 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-59e7dd36a87c4fc18878127771ded28a
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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