Pyridine → HCID 10643600, compound

HRID 2395195Notes

Reaction equation

HRID 2395195 reaction equation
[F:1][C:2]([F:15])([CH:12]([F:14])[F:13])[CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.N1C=CC=[CH:18][CH:17]=1.Cl[C:23]([O:25][C:26]1[CH:31]=CC=CC=1)=[O:24].FC(F)(C(F)F)COC1C=C[C:39]([NH:42][C:43](=O)[O:44]C2C=CC=CC=2)=CC=1>ClCCl>[CH2:26]([O:25][CH:23]([O:24][CH2:17][CH3:18])[CH2:39][NH:42][C:43]([NH:9][C:8]1[CH:10]=[CH:11][C:5]([O:4][CH2:3][C:2]([F:15])([F:1])[CH:12]([F:13])[F:14])=[CH:6][CH:7]=1)=[O:44])[CH3:31]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 15891Phenyl chloroformateHCID 10497536HCID 10497536, compoundHCID 187663254-(2,2,3,3-Tetrafluoropropoxy)aniline

Product 1

HCID 10643600HCID 10643600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2,2,3,3-tetrafluoropropoxy)aniline (25 g) and pyridine (25.2 g) were dissolved in 200 ml of dichloromethane and, under ice-cooling, 33.3 g of phenyl chloroformate was added dropwise to the solution. After stirring under ice-cooling for 30 minutes, the reaction mixture was washed with water, dried and the solvent was distilled off to give a mixture of phenyl 4-(2,2,3,3-tetrafluoropropoxy)phenylcarbamate and pyridine. To the mixture was added 30.7 g of 2-(diethoxy)ethylamine, and the resultant mixture was stirred at room temperature. The precipitated crystals were collected by filtration and washed with petroleum ether to give 37.8 g of N-(2,2-diethoxyethyl)-N'-[4-(2,2,3,3-tetrafluoropropoxy)phenyl] urea as colorless crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. washthe reaction mixture was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customto give
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with petroleum ether

Sources & evidence

ORD record
ord-711dd6d754374357b026126ddb7c1ece
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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