Triethylamine → 2-[1-(5-Bromo-3-Thienyl)-2-Nitroethyl]-4-(p-Chlorophenyl)-2-(Trifluoromethyl)-3-Oxazolin-5-One

HRID 2396547Notes

Reaction equation

HRID 2396547 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19](=[O:20])[O:18][CH:17]([C:21]([F:24])([F:23])[F:22])[N:16]=2)=[CH:11][CH:10]=1.[Br:25][C:26]1[S:27][CH:28]=[C:29]([CH:31]=[CH:32][N+:33]([O-:35])=[O:34])[CH:30]=1>C1(C)C=CC=CC=1.Cl.CCOCC>[Br:25][C:26]1[S:27][CH:28]=[C:29]([CH:31]([C:17]2([C:21]([F:22])([F:24])[F:23])[N:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=3)[C:19](=[O:20])[O:18]2)[CH2:32][N+:33]([O-:35])=[O:34])[CH:30]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 110652915(2H)-Oxazolone, 4-(4-chlorophenyl)-2-(trifluoromethyl)-HCID 540979492-Bromo-4-(2-nitrovinyl)thiophene

Product 1

HCID 194192982-[1-(5-Bromo-3-Thienyl)-2-Nitroethyl]-4-(p-Chlorophenyl)-2-(Trifluoromethyl)-3-Oxazolin-5-One

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of triethylamine (0.30 g, 3 mmol) in toluene is added to a solution of 4-(p-chlorophenyl)-2-(trifluoromethyl)-3-oxazolin-5-one (10.00 g, 38 mmol) and 2-bromo-4-(2-nitrovinyl)thiophene (8.98 g, 32 mmol) in toluene at 0° C. The reaction mixture is warmed to room temperature and diluted with dilute hydrochloric acid and ether. The organic layer is separated, dried over MgSO4, concentrated in vacuo, diluted with hexane, stirred at reflux, cooled to room temperature and decanted to obtain a clear solution. The solution is concentrated in vacuo and chromatographed to give the title product.

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. additiondiluted with hexane
  5. temperatureat reflux
  6. temperaturecooled to room temperature
  7. customdecanted
  8. customto obtain a clear solution
  9. concentrationThe solution is concentrated in vacuo
  10. customchromatographed

Sources & evidence

ORD record
ord-afbb082226d241a0b9f6ebad82186e03
Source dataset
uspto-grants-1996_02
Patent number
US05492925

Reaction notes

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