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

HRID 273771

反応式

HRID 273771 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-8da25c14880748e7b03a2bd4e34653fd
出典データセット
uspto-grants-1995_02
特許番号
US05387599

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