Pyridine → 2-(m-Trifluoromethylphenyl)-3-(3-trifluoromethylbutyroyl)-5-ethyl-1,3-oxazolidine

HRID 621381Notes

Reaction equation

HRID 621381 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]2[NH:13][CH2:12][CH:11]([CH2:14][CH3:15])[O:10]2)[CH:6]=[CH:7][CH:8]=1.N1C=CC=CC=1.[F:24][C:25]([F:33])([F:32])[CH:26]([CH3:31])[CH2:27][C:28](Cl)=[O:29].[OH-].[Na+]>C(Cl)Cl.O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]2[N:13]([C:28](=[O:29])[CH2:27][CH:26]([C:25]([F:33])([F:32])[F:24])[CH3:31])[CH2:12][CH:11]([CH2:14][CH3:15])[O:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 212424864,4,4-Trifluoro-3-methylbutanoyl chlorideHCID 212424932-(m-Trifluoromethylphenyl)-5-ethyl-1,3-oxazolidine

Product 1

HCID 212424872-(m-Trifluoromethylphenyl)-3-(3-trifluoromethylbutyroyl)-5-ethyl-1,3-oxazolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Three and eight-tenths grams of 2-(m-trifluoromethylphenyl)-5-ethyl-1,3-oxazolidine was combined with 1.3 g of pyridine in 25 ml of methylene chloride and 2.7 g of 3-trifluoromethylbutyroyl chloride in 10 ml of methylene chloride was added dropwise with stirring. The mixture was allowed to stand overnight and was stand overnight and was worked up with 50 ml of 5% NaOH and 200 ml of water. The mixture was dried and stripped under vacuum on the rotary evaporator. The structure was confirmed by NMR and infrared spectroscopy.

Workup

  1. additionwas added dropwise
  2. waitwas stand overnight
  3. customThe mixture was dried
  4. customstripped under vacuum on the rotary evaporator

Sources & evidence

ORD record
ord-842df48eda8c4bceb073cee2da5625b1
Source dataset
uspto-grants-1989_04
Patent number
US04824468

Reaction notes

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