Potassium Carbonate → N-(2-Bromophenyl)cinnamamide

HRID 1056051Notes

Reaction equation

HRID 1056051 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C([O-])([O-])=O.[K+].[K+].[C:15](Cl)(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.CC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:15](=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 119922-BromoanilineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 764332N-(2-Bromophenyl)cinnamamideYield 64%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-bromoaniline (0.976 g, 5.81 mmol, Sigma-Aldrich) and K2CO3 (1.16 g, 8.71 mmol) in water (5.5 mL) and acetone (4.5 mL) was added cinnamoyl chloride (1 g, 5.81 mmol, Sigma-Aldrich) and the reaction was stirred for 2 h at 0° C. The mixture was treated with ice cold water (25 mL) to obtain a brownish precipitate. The precipitate was filtered and dried under vacuum. The crude material was further treated with petroleum ether to give N-(2-bromophenyl)cinnamamide (1.1 g, 64%) as off-white solid. MS (ESI, pos. ion) m/z: 303.2 (M+1).

Workup

  1. customto obtain a brownish precipitate
  2. filtrationThe precipitate was filtered
  3. customdried under vacuum
  4. additionThe crude material was further treated with petroleum ether

Sources & evidence

ORD record
ord-e5bccb47e001461dbbdf352ff3cb302a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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