N-chloroacetyl-N-ethoxycarbonylmethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline → 1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2,5-piperazinedione

HRID 1077898Notes

Reaction equation

HRID 1077898 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:20][C:21]([O:23]CC)=O)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([F:19])([F:18])[CH:15]([F:17])[F:16])=[CH:8][CH:7]=1)=[O:4].[NH3:26].C(O)C>>[F:18][C:14]([F:19])([CH:15]([F:17])[F:16])[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[CH2:20][C:21](=[O:23])[NH:26][CH2:2][C:3]2=[O:4])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 19065094N-chloroacetyl-N-ethoxycarbonylmethyl-4-(2,2,3,3-tetrafluoropropoxy)anilineHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 190651201-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2,5-piperazinedione

Conditions

Temperature
60 °C

Procedure

The resulting N-chloroacetyl-N-ethoxycarbonylmethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline (1.9 g) was dissolved in 20 ml of 10.5% ammonia-ethanol and the solution was stirred at 60° C. for four hours. After cooling, the crystals separated out therefrom were collected by filtration and washed with cold ethanol to give 1.5 g of 1-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,5-piperazinedione as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. customthe crystals separated out
  3. filtrationtherefrom were collected by filtration
  4. washwashed with cold ethanol

Sources & evidence

ORD record
ord-1dd724f3934f4036837f7f0a3e6e494b
Source dataset
uspto-grants-1996_08
Patent number
US05545652

Reaction notes

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