Pyridine → N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea

HRID 129157Notes

Reaction equation

HRID 129157 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=[CH:12][CH:11]=1.Cl[C:17]([O:19][C:20]1[CH:25]=CC=CC=1)=[O:18].FC1C=C(F)C=C[C:28]=1[NH:34][C:35](=O)[O:36]C1C=CC=CC=1>ClCCl>[CH2:20]([O:19][CH:17]([O:18][CH2:11][CH3:12])[CH2:28][NH:34][C:35]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[F:1])=[O:36])[CH3:25]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 97092,4-DifluoroanilineHCID 15891Phenyl chloroformateHCID 13733129phenyl N-(2,4-difluorophenyl)carbamate

Product 1

HCID 19065111N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-difluoroaniline (25g) and 25.2 g of pyridine were dissolved in 200 ml of dichloromethane to which was added dropwise 33.3 g of phenyl chloroformate with ice cooling. After stirring for 30 minutes with ice cooling, the reaction solution was washed with water and dried followed by distilling the solvent to give a mixture of phenyl 2,4-difluorophenylcarbamate and pyridine. To the mixture was added 30.7 g of 2-(di-ethoxy)ethylamine and the mixture was stirred at room temperature. The crystals separated out were filtered and washed with petroleum ether to give 37.8 g of N-(2,2-diethoxyethyl)-N'-(2,4-difluorophenyl)urea as colorless crystals.

Workup

  1. washthe reaction solution was washed with water
  2. customdried
  3. distillationby distilling the solvent
  4. customto give
  5. stirringthe mixture was stirred at room temperature
  6. customThe crystals separated out
  7. filtrationwere filtered
  8. washwashed with petroleum ether

Sources & evidence

ORD record
ord-458278adf92941f1a13d84297af8e95b
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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