4-Bromophenyl isocyanate → 4-[3-(4-Bromo-phenyl)-ureido]-N,N-dimethyl-benzamide

HRID 2092514Notes

Reaction equation

HRID 2092514 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>C(Cl)Cl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:22])[NH:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 756094-Bromophenyl isocyanateHCID 2355274-Amino-N,N-dimethylbenzamide

Product 1

HCID 689172644-[3-(4-Bromo-phenyl)-ureido]-N,N-dimethyl-benzamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-N,N-dimethyl-benzamide (3.5 g, 0.0213 mol), TEA (2.15 g, 0.0213 mol) in DCM (50 mL) was added 4-bromophenyl isocyanate (5.07 g, 0.0256 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 [6.8 g, 88%]; LC-MS (ESI): Calculated mass: 361.0; Observed mass: 362.0 [M+H]+ (RT: 0.17 min).

Workup

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

Sources & evidence

ORD record
ord-526d5903a1ba42cfb6e73a84c3b2cb06
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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