Butyl-p-toluenesulfonate → Hydrochloric Acid

HRID 370556

Reaction equation

HRID 370556 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:18])([CH2:16][SH:17])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].[C:21]1(C)[CH:26]=CC(S(OCCCC)(=O)=O)=[CH:23][CH:22]=1>CN(C)C=O.O>[CH2:26]([S:17][CH2:16][C@:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([OH:18])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)[CH2:21][CH2:22][CH3:23].[ClH:1]

Participants

7

Reactant 3

HCID 13066Butyl-p-toluenesulfonateHCID 24758Sodium hydrideHCID 13420610(R)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-mercapto-2-propanol

Product 2

HCID 313Hydrochloric AcidYield 1,386%HCID 13420611(R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-mercapto-2-propanol (II) (3 g) in dry N,N-dimethylformamide (20 ml) were added a 50% dispersion of sodium hydride in paraffin (1 g) and n-butyl p-toluenesulfonate (2.3 g) at 0°-5° C. in nitrogen atmosphere. The mixture was stirred at 0°-5° C. for 1 hour and at 20°-25° C. for 18 hours. The reaction mixture was diluted with water (200 ml) and extracted with dichloromethane. Treatment of the extract in the same manner as in Example 4 gave (R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (I: n=3) hydrochloride (2.5 g). Yield, 63.8%. M.P., 168°-169° C. [α]D20 -88.8° (c=1, methanol).

Workup

  1. extractionextracted with dichloromethane
  2. extractionTreatment of the extract in the same manner as in Example 4

Sources & evidence

ORD record
ord-5de86fa94cf0496f835b0e09c317dae8
Source dataset
uspto-grants-1985_07
Patent number
US04526983

Linked notes

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