2-Mercaptoethanol → HCID 10568353, compound

HRID 2395686Notes

Reaction equation

HRID 2395686 reaction equation
[H-].[Na+].[SH:3][CH2:4][CH2:5][OH:6].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C@@:15]1([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[C@H:17]([CH3:18])[O:16]1>CCCCCC.CN(C)C=O.C(OCC)(=O)C>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C@:15]([OH:16])([C@H:17]([S:3][CH2:4][CH2:5][OH:6])[CH3:18])[CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1

Participants

7

Reactant 3

HCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-

Product 1

HCID 10568353HCID 10568353, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

70 mg (1.60 mmole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were washed with hexane, and then suspended in 3 ml of dimethylformamide. 187 mg (2.4 mmole) of 2-mercaptoethanol were added to the resulting suspension under an atmosphere of nitrogen, whilst ice-cooling, and the mixture was stirred for 10 minutes. At the end of this time, 200 mg (0.80 mmole) of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (prepared as described in European Patent Publication 332 387, the disclosure of which is incorporated herein by reference) were added to the mixture, and the resulting mixture was stirred at 50°-60° C. for 30 minutes. The mixture was then cooled after which it was diluted with ethyl acetate. It was then washed with a saturated aqueous solution of sodium chloride; and the solvent was then removed by distillation under reduced pressure. The crude product thus obtained was purified by column chromatography through 10 g of silica gel, using a 4:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 195 mg of the title compound. A pure specimen melting at 89°-90° C. was then obtained by recrystallization from a mixture of ethyl acetate and hexane.

Workup

  1. temperaturecooling
  2. additionwere added to the mixture
  3. stirringthe resulting mixture was stirred at 50°-60° C. for 30 minutes
  4. temperatureThe mixture was then cooled after which it
  5. washIt was then washed with a saturated aqueous solution of sodium chloride
  6. customand the solvent was then removed by distillation under reduced pressure
  7. customThe crude product thus obtained
  8. customwas purified by column chromatography through 10 g of silica gel
  9. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-083c52e8e2b84f2fa4b23167546c22ec
Source dataset
uspto-grants-1996_02
Patent number
US05489606

Reaction notes

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