Chloromethyl methyl sulfide → HCID 54478809, compound

HRID 2395690Notes

Reaction equation

HRID 2395690 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@:11]([OH:21])([C@H:18]([SH:20])[CH3:19])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1.[H][H].[CH3:24][S:25][CH2:26]Cl>CCCCCC.CN(C)C=O>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@:11]([OH:21])([C@H:18]([S:20][CH2:24][S:25][CH3:26])[CH3:19])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

7

Reactant 4

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 1922642-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanolHCID 178418361HCID 178418361, compound

Product 1

HCID 54478809HCID 54478809, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

31 mg (0.70 mmole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were washed with anhydrous hexane and then suspended in 2 ml of dimethylformamide. 100 mg (0.35 mmole) of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol were then added at 0° C., with stirring, to the resulting suspension. After evolution of hydrogen gas had ceased, 67 mg (0.70 mmole) of methylthiomethyl chloride were added to the mixture. The resulting mixture was then stirred at the same temperature for 1 hour. At the end of this time, the reaction mixture was partitioned between ethyl acetate and an aqueous solution of sodium chloride. The organic layer was dried and concentrated by distilling off the solvent. The crude product thus obtained was purified by column chromatography through silica gel, using a 3:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 105 mg of the title compound as a solid. A pule specimen (78 mg), melting at 108°-109° C., was obtained by recrystallization of this solid from a mixture of ethyl acetate and hexane.

Workup

  1. stirringThe resulting mixture was then stirred at the same temperature for 1 hour
  2. customAt the end of this time, the reaction mixture was partitioned between ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. distillationby distilling off the solvent
  6. customThe crude product thus obtained
  7. customwas purified by column chromatography through silica gel
  8. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-ac266cd426544ad6b9fd910809752bd6
Source dataset
uspto-grants-1996_02
Patent number
US05489606

Reaction notes

Loading…