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

HRID 1654231Notes

Reaction equation

HRID 1654231 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.COC(=O)CC[SH:23].[H-].[Na+].Cl>O.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:23])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 18050Methyl 3-mercaptopropionateHCID 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 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the solution of 2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (8.0 g) and 3-mercaptopropionic acid methyl ester (11.2 ml) in dimethylformaide (160 ml) was added 60% sodium hydride suspension in oil (4.0 g), and the mixture was stirred for 15 minutes. 1N aqueous hydrochloric acid solution (101 ml) was added dropwise to adjust pH to 7, and dimethylformamide and water were evaporated off under reduced pressure. To the residue was added 20 ml of water, followed by extraction with ethyl acetate (50 ml×3). The extract was washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography (6.0×9.0 cm) and eluted with ethyl acetate-hexane (3:1). The desired fraction was concentrated, and to the residue was added diethyl ether, to give 2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (6.44 g) as colorless needles. mp. 112°-113° C.

Workup

  1. customwere evaporated off under reduced pressure
  2. additionTo the residue was added 20 ml of water
  3. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfollowed by evaporation under reduced pressure
  7. washeluted with ethyl acetate-hexane (3:1)
  8. concentrationThe desired fraction was concentrated
  9. additionto the residue was added diethyl ether

Sources & evidence

ORD record
ord-b12f9642c1bd458f9d01053920e66ab9
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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