Dimethyl Sulfoxide → HCID 15016299, compound

HRID 2106617Notes

Reaction equation

HRID 2106617 reaction equation
[Na].CS(C)=O.[OH:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:8]=1.Br[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)C>[CH2:27]([O:26][C:24]([CH:23]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=2)[N:8]=1)[CH3:29])=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178517999HCID 178517999, compound

Product 1

HCID 15016299HCID 15016299, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.54 g portion of sodium was dissolved in 15 ml of absolute ethanol, and was added to 50 ml of dimethylsulfoxide containing 5.4 g of 3-hydroxy-1-(4-trifluoromethylphenyl)-1,2,4-1H-triazole. An additional 25 ml of dimethylsulfoxide was added, and the mixture was heated on the steam bath for 15 minutes. Then 4.3 g of ethyl 2-bromopropionate was added and heating was continued for 1 hour. The mixture was then cooled and poured over ice-water, and the product was collected, dried, and purified by high-performance liquid chromatography, eluting with 1:1 hexane:ethyl acetate. The product-containing fractions were combined and evaporated under vacuum to obtain 3.5 g of the desired product.

Workup

  1. temperaturethe mixture was heated on the steam bath for 15 minutes
  2. temperatureheating
  3. temperatureThe mixture was then cooled
  4. customthe product was collected
  5. customdried
  6. custompurified by high-performance liquid chromatography
  7. washeluting with 1:1 hexane
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-a3dac636a1e7480d988a99d0e1165323
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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