1,2,4-Trichlorobenzene → Fenuron

HRID 2372526Notes

Reaction equation

HRID 2372526 reaction equation
[CH3:1][N:2]([CH3:6])[C:3]([NH2:5])=[O:4].N[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.ClC1C=CC(Cl)=CC=1Cl.CNC>>[C:8]1([NH:5][C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 131,2,4-TrichlorobenzeneHCID 674Dimethylamine2×HCID 6115AnilineHCID 11737N,N-Dimethylurea

Product 1

HCID 7560Fenuron

Conditions

Temperature
205 °C

Procedure

3.35 g (0.038 mol) of N,N-dimethylurea and 2.33 g (0.025 mol) of aniline were added with stirring into 28 ml of 1,2,4-trichlorobenzene. The reaction mixture was slowly heated to 205° C., dimethylamine being passed in from 60° C. After 5.5 hours, 11.8 g (0.27 mol) of dimethylamine had been passed in and the reaction was complete. The reaction mixture was cooled to room temperature, whereupon a precipitate deposited. The precipitate was filtered off, washed with 1,2,4-trichlorobenzene, dried and then boiled in water. The aqueous mixture was cooled, and the precipitate was filtered off with suction and dried. 3.3 g of N-phenyl-N',N'-dimethylurea, i.e. 81% of theory, having a melting point of 130° to 133° C. were obtained in this way.

Workup

  1. custompassed in from 60° C
  2. temperatureThe reaction mixture was cooled to room temperature, whereupon a precipitate
  3. filtrationThe precipitate was filtered off
  4. washwashed with 1,2,4-trichlorobenzene
  5. customdried
  6. temperatureThe aqueous mixture was cooled
  7. filtrationthe precipitate was filtered off with suction
  8. customdried
  9. customwere obtained in this way

Sources & evidence

ORD record
ord-a90aec671b7f48f086e7eb909e2a8e52
Source dataset
uspto-grants-1992_03
Patent number
US05099021

Reaction notes

Loading…