1,2,4-Trichlorobenzene → Urea, N'-(4-bromophenyl)-N,N-dimethyl-

HRID 2372524Notes

Reaction equation

HRID 2372524 reaction equation
[CH3:1][N:2]([CH3:6])[C:3]([NH2:5])=[O:4].[Br:7][C:8]1[CH:14]=[CH:13][C:11](N)=[CH:10][CH:9]=1.ClC1C=CC(Cl)=CC=1Cl.CNC>>[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH:5][C:3]([N:2]([CH3:6])[CH3:1])=[O:4])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 131,2,4-TrichlorobenzeneHCID 674Dimethylamine2×HCID 78074-BromoanilineHCID 11737N,N-Dimethylurea

Product 1

HCID 18870Urea, N'-(4-bromophenyl)-N,N-dimethyl-

Conditions

Temperature
205 °C

Procedure

3.35 g (0.038 mol) of N,N-dimethylurea and 4.3 g (0.025 mol) of 4-bromoaniline were added with stirring into 28 ml of 1,2,4-trichlorobenzene, after which the mixture was slowly heated to 205° C. Dimethylamine was introduced from 50° C. After 5.5 hours, 11.6 g (0.25 mol) of dimethylamine had been introduced, and the reaction was complete. The reaction mixture was cooled to room temperature whereupon a precipitate deposited, which was filtered off, washed with 1,2,4-trichlorobenzene, dried at 100° C. in vacuo and then boiled in 100 ml of water. The aqueous mixture was cooled, and the precipitate was filtered off with suction and dried. 4.73 g of N-(4-bromophenyl)-N',N'-dimethylurea, i.e. 78% of theory, having a melting point of 168° to 170° C. were obtained in this way.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature whereupon a precipitate
  2. filtrationwhich was filtered off
  3. washwashed with 1,2,4-trichlorobenzene
  4. customdried at 100° C. in vacuo
  5. temperatureThe aqueous mixture was cooled
  6. filtrationthe precipitate was filtered off with suction
  7. customdried
  8. customwere obtained in this way

Sources & evidence

ORD record
ord-c38bc2fa80a24675a8005dafcc542420
Source dataset
uspto-grants-1992_03
Patent number
US05099021

Reaction notes

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