3,4-Dichloroaniline → Monomethyldiuron

HRID 442284Notes

Reaction equation

HRID 442284 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[CH3:10][N:11]=[C:12]=[O:13]>C(OC(C)C)(C)C>[CH3:10][NH:11][C:12]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=1)=[O:13]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 12228Methyl Isocyanate

Product 1

HCID 19113Monomethyldiuron

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 27.4 g of 3,4-dichloroaniline in 140 ml of isopropyl ether was added slowly to 9 g of methyl isocyanate in 100 ml of isopropyl ether and the mixture was refluxed for 2 hours and was then cooled to 0° C. The precipitate formed was recovered by vacuum filtration and was washed with isopropyl ether. The mother liquors were concentrated to obtain a second crop. The two combined crops weighing 19.5 g and melting at 156° C. were crystallized from ethyl acetate to obtain N-methyl-N'-(3,4-dichlorophenyl)-urea melting at 160° C., identical to the product described by Onley et al., J. Ass. Off. Anal. Chem., Vol. 52 (1969), p. 545.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe precipitate formed
  3. filtrationwas recovered by vacuum filtration
  4. washwas washed with isopropyl ether
  5. concentrationThe mother liquors were concentrated
  6. customto obtain a second crop
  7. customwere crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2745c61cefa6423186a6d4f99f69362c
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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