Iodine → HCID 9829484, compound

HRID 1645829Notes

Reaction equation

HRID 1645829 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:19])([CH:16]([SH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.II>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:19])([CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)[CH:16]([S:18][S:18][CH:16]([C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([OH:19])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)[CH3:17])[CH3:17]

Participants

4

Reactant 2

HCID 807IodineHCID 9882302(2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 9829484HCID 9829484, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To dichloromethane (20 ml) was added (2RS,3RS)-2(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol (0.3 g). To the mixture was added dropwise at room temperature a dichloromethane solution (10 ml) of iodine (0.17 g). The mixture was stirred for 30 minutes at room temperature, washed with a 5% aqueous solution of sodium hydrogensulfite and dried (Na2SO4). The solvent was then distilled off under reduced pressure. The residue was subjected to a silica gel chromatography (2.5×30 cm), eluting with ethyl acetate - hexane (4:1). The objective fraction was concentrated. Addition of diethyl ether-hexane (2:1) to the concentrate gave bis[3-(2,4- difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2butyl] disulfide (Compound 15, 0.15 g) as a colorless powder.

Workup

  1. washwashed with a 5% aqueous solution of sodium hydrogensulfite
  2. dry with materialdried (Na2SO4)
  3. distillationThe solvent was then distilled off under reduced pressure
  4. washeluting with ethyl acetate - hexane (4:1)
  5. concentrationThe objective fraction was concentrated
  6. additionAddition of diethyl ether-hexane (2:1) to the concentrate

Sources & evidence

ORD record
ord-94ab966cd84b4040957360da39e252cf
Source dataset
uspto-grants-1993_01
Patent number
US05177094

Reaction notes

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