Diisopropyl Ether → N-methyl-N'-n-butyl-N'-(3,4-dichlorophenyl)-urea

HRID 442295Notes

Reaction equation

HRID 442295 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[CH2:2][CH2:3][CH3:4].C(OC(C)C)(C)C.[CH3:21][N:22]=[C:23]=[O:24]>C(N(CC)CC)C>[CH3:21][NH:22][C:23]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:24]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 12228Methyl IsocyanateHCID 29276966N-Butyl-3,4-dichloroaniline

Product 1

HCID 21499778N-methyl-N'-n-butyl-N'-(3,4-dichlorophenyl)-ureaYield 46.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 100 g of N-n-butyl-3,4-dichloroaniline (described in West German Pat. No. 1,902,419), 250 ml of isopropyl ether, 10 ml of triethylamine and 60 g of methyl isocyanate was stirred for 18 hours at room temperature and the solvent was distilled off under reduced pressure. The residue was added to petroleum ether (b.p.=65°-75° C.) and after cooling, the precipitate formed was recovered by vacuum filtration to obtain 59 g of N-methyl-N'-n-butyl-N'-(3,4-dichlorophenyl)-urea melting at 58° C.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was added to petroleum ether (b.p.=65°-75° C.)
  3. temperatureafter cooling
  4. customthe precipitate formed
  5. filtrationwas recovered by vacuum filtration

Sources & evidence

ORD record
ord-d74711646b814fdca9da5636f0484bb6
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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