Sodium hydride → 2-(2,4-dichlorophenyl)-3-(piperidinosulphonylmethylthio)-1-(1H-1,2,4-triazol-1-yl)-propan-2-ol

HRID 1381136Notes

Reaction equation

HRID 1381136 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[CH2:10][SH:11].[H-].[Na+].Cl[CH2:22][S:23]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=[O:25])=[O:24]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:10][S:11][CH2:22][S:23]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=[O:25])=[O:24])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15199361-Chloromethanesulfonyl-piperidineHCID 202058911-[2-(2,4-dichlorophenyl)-2-hydroxy-3-mercaptopropyl]-1H-1,2,4-triazole

Product 1

HCID 233237662-(2,4-dichlorophenyl)-3-(piperidinosulphonylmethylthio)-1-(1H-1,2,4-triazol-1-yl)-propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2,4-Dichlorophenyl)-1-mercapto-3-(1H-1,2,4-triazol-1-yl)-propan-2-ol (0.304 g) was stirred in tetrahydrofuran (5 ml) whilst sodium hydride (58 mg of a 50% dispersion in oil, 1.2 equiv.) was added in one portion. After stirring a further five minutes, N-(chloro-methylsulphonyl)piperidine (0.296 g, 1.1 equiv.) was added and heated under reflux for 3 hours. The reaction mixture was allowed to cool to room temperature then poured into an ice/water mixture (20 ml), and extracted with ethyl acetate (3×15 ml). The organic extracts were combined, dried (Na2SO4) and evaporated to a gum, 0.71 g.

Workup

  1. additionwas added in one portion
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. extractionextracted with ethyl acetate (3×15 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to a gum, 0.71 g

Sources & evidence

ORD record
ord-99ee1edd967a47e1ad32ab9bec084933
Source dataset
uspto-grants-1986_04
Patent number
US04585778

Reaction notes

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