4-Bromophenyl isocyanate → 4-(3-(4-bromophenyl)ureido)-2-fluoro-N,N-dimethyl-benzamide

HRID 517431Notes

Reaction equation

HRID 517431 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[C:4]([F:13])[CH:3]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>C(Cl)Cl>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:23])[NH:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[C:4]([F:13])[CH:3]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 756094-Bromophenyl isocyanateHCID 580578764-amino-2-fluoro-N,N-dimethylbenzamide

Product 1

HCID 675151244-(3-(4-bromophenyl)ureido)-2-fluoro-N,N-dimethyl-benzamideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round bottom flask, 4-amino-2-fluoro-N,N-dimethyl-benzamide (2.5 g, 0.0137 mol), 4-bromophenylisocyanate (3.3 g, 0.0164), TEA (3.9 mL, 0.0274 mol) and DCM (50 mL) was added. The reaction mixture was stirred at room temperature for 12 h. After 12 h, the precipitate was formed and was collected by filtration. The solid was washed with diethyl ether and dried to get the title compound [3.0 g, 58%]. Calculated mass: 379.0; Observed mass: 380.0 (RT: 1.46 min). This compound was directly taken to the next step.

Workup

  1. waitAfter 12 h
  2. customthe precipitate was formed
  3. filtrationwas collected by filtration
  4. washThe solid was washed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-215fdb69aa8d4b08adcba57c3bab856d
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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