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

HRID 1654170Notes

Reaction equation

HRID 1654170 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH:11]([CH3:12])[O:10]1.[SH:19]CCC(OC)=O.C[O-].[Na+].CO.Cl>O.CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH:11]([SH:19])[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 18050Methyl 3-mercaptopropionateHCID 147064491-((2-(2,4-Difluorophenyl)-3-methyl-2-oxiranyl)methyl)-1H-1,2,4-triazoleHCID 23694274Sodium methanolate methanol

Product 1

HCID 9882302(2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A methanol (2.0 ml) solution containing (2RS,3RS)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (0.05 g), methyl 3-mercaptopropionate (0.11 ml) and a 28% sodium methylate-methanol solution (0.14 ml) was refluxed for 1.0 hour. The reaction mixture was cooled, to which was added water (10 ml). The mixture was neutralized with 1N aqueous solution of hydrochloric acid, followed by extraction with methylene chloride (5.0 ml×twice). The extract solution was dried over anhydrous sodium sulfate, then the solvent was distilled off. The residue was subjected to a silica gel chromatography (2.5 cm×5 cm), followed by elution with ethyl acetate-hexane (1:2). The object fraction was concentrated, to which was added ethyl acetate to give (2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-[(1H)-1,2,4-triazol-1-yl]-2-butanol (0.030 g) as colorless needles.

Workup

  1. temperatureThe reaction mixture was cooled, to which
  2. extractionfollowed by extraction with methylene chloride (5.0 ml×twice)
  3. dry with materialThe extract solution was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. washfollowed by elution with ethyl acetate-hexane (1:2)
  6. concentrationThe object fraction was concentrated, to which
  7. additionwas added ethyl acetate

Sources & evidence

ORD record
ord-7da100a16d3f4b46b528ce38555e4cb7
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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