Carbon Dioxide → HCID 15753030, compound

HRID 1086620Notes

Reaction equation

HRID 1086620 reaction equation
[CH2:1]([N:3](CC)CC)C.[C:8]1([C:14]2[C:18](=O)O[CH:16]([C:20]([F:23])([F:22])[F:21])[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:25](=C)C#N.C(=O)=O>O.C(#N)C>[C:8]1([C:14]2[NH:15][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:25][C:18]=2[C:1]#[N:3])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 27409315(2H)-Oxazolone, 4-phenyl-2-(trifluoromethyl)-

Product 1

HCID 15753030HCID 15753030, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Triethylamine (4.5 g, 0.044 mol) is added dropwise to a mixture of 4-phenyl-2-(trifluoromethyl)-5(2H)-oxazolone (10.0 g, 0.043 mol), 2-chloroacrylonitrile (3.51 g, 0.43 mol) and acetonitrile (50 mL). The temperature of the reaction mixture rises to 65° C. and carbon dioxide gas evolves during the addition. After the addition is complete the reaction mixture is heated at reflux temperature for one hour, cooled to room temperature and poured into water (150 mL). The solids are collected by filtration, air-dried and dried under vacuum at 60° C. to give the title compound as a white solid (10.05 g, 97%). Identified by NMR spectral analyses.

Workup

  1. customrises to 65° C.
  2. additionAfter the addition
  3. temperatureis heated
  4. temperatureat reflux temperature for one hour
  5. filtrationThe solids are collected by filtration
  6. customair-dried
  7. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-5185342ad2544ceabdac3a36ff3db49e
Source dataset
uspto-grants-1991_07
Patent number
US05030735

Reaction notes

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