Hydrochloric Acid → 2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 1654168Notes

Reaction equation

HRID 1654168 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:11][O:10]1.[SH:18]CCC(O)=O.[H-].[Na+].Cl>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH2:11][SH:18])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 65143-Mercaptopropionic AcidHCID 24758Sodium hydrideHCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazole

Product 1

HCID 200795622-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dimethylformamide (160 ml) solution of 2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)oxirane (8.0 g) and methyl ester of 3-mercaptopropionic acid was added, under ice-cooling, 60% sodium hydride (4.0 g). The mixture was stirred for 15 minutes, to which was added dropwise a 1N aqueous solution of hydrochloric acid (101 ml) to adjust the pH to 7, followed by distilling off dimethylformamide and water. To the residue was added water (20 ml), which was extracted with ethyl acetate (50 ml×3). The extract was washed with a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, followed by distilling off the solvent. The residue was subjected to a silica gel chromatography (6.0×9.0 cm), followed by elution with ethyl acetate-hexane (3:1). The object fraction was concentrated, to which was added diethyl ether to afford 2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (6.44 g) as colorless needles, m.p. 112°-113° C.

Workup

  1. temperaturecooling
  2. distillationby distilling off dimethylformamide and water
  3. additionTo the residue was added water (20 ml), which
  4. extractionwas extracted with ethyl acetate (50 ml×3)
  5. washThe extract was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationby distilling off the solvent
  8. washfollowed by elution with ethyl acetate-hexane (3:1)
  9. concentrationThe object fraction was concentrated, to which
  10. additionwas added diethyl ether

Sources & evidence

ORD record
ord-84b6a0298a46454abf59fefb3d5a975d
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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