4-Chloroaniline → 2,3-Dibromo-N-[(4-chlorophenyl)carbamoyl]propanamide

HRID 259167Notes

Reaction equation

HRID 259167 reaction equation
[Br:1][CH:2]([CH2:8][Br:9])[C:3]([N:5]=[C:6]=[O:7])=[O:4].[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>C1C=CC=CC=1>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:6]([NH:5][C:3](=[O:4])[CH:2]([Br:1])[CH2:8][Br:9])=[O:7])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 203185382,3-Dibromopropanoyl isocyanate

Product 1

HCID 214233172,3-Dibromo-N-[(4-chlorophenyl)carbamoyl]propanamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 54 g of 2,3-dibromopropionyl isocyanate in 100 ml of benzene is added dropwise with cooling at 20° C. to a solution of 25 g of 4-chloroaniline in 250 ml of dry benzene. After stirring for 3 hours at 20° C., the suspension is diluted with 200 ml of petroleum ether, filtered and dried. Yield: 71.0 g, m.p.: 162° - 163° C.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-0bf7e1cf6e304ad3b1ee57180cedaae7
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

Loading…