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Dichloromethane → [(2RS,3RS)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2butyl] N,N-diethyldithiocarbamate

HRID 273771
Notes
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Reaction equation

HRID 273771 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.ClCCl.C(N(CC)CC)C.[CH2:30]([N:32]([CH2:36][CH3:37])[C:33](Cl)=[S:34])[CH3:31]>O>[CH2:30]([N:32]([CH2:36][CH3:37])[C:33](=[S:34])[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])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 66607Diethylthiocarbamoyl chlorideHCID 9882302(2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 20094307[(2RS,3RS)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2butyl] N,N-diethyldithiocarbamateYield 30.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-[1H-1,2,4-triazol-1-yl]-2-butanol (0.3 g) was added to dichloromethane (5 ml), to which triethylamine (0.16 ml) was added under ice-cooling, and then, N,N-diethylthiocarbamoyl chloride (0.18 g) was added. The resultant solution was stirred for 1 hour at room temperature. Thereafter, water (20 ml) was added to the reaction mixture. The resultant mixture was then extracted with dichloromethane (40 ml). The extract was washed with water (20 ml), dried (MgSO4) and distilled off to remove the solvent under reduced pressure. The residue was purified by a silica gel column chromatography (2.9×30cm, eluent: ethyl acetate-dichloromethane=1:3). The objective fractions were concentrated. Hexane was added to the residue to give the compound (1), i.e., [(2RS,3RS)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2butyl] N,N-diethyldithiocarbamate (0.13 g) as colorless needles.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionThe resultant mixture was then extracted with dichloromethane (40 ml)
  4. washThe extract was washed with water (20 ml)
  5. dry with materialdried (MgSO4)
  6. distillationdistilled off
  7. customto remove the solvent under reduced pressure
  8. customThe residue was purified by a silica gel column chromatography (2.9×30cm, eluent: ethyl acetate-dichloromethane=1:3)
  9. concentrationThe objective fractions were concentrated
  10. additionHexane was added to the residue

Sources & evidence

ORD record
ord-8da25c14880748e7b03a2bd4e34653fd
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387599

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes