Hydrochloric Acid → Hydrochloric Acid

HRID 370555Notes

Reaction equation

HRID 370555 reaction equation
[OH-].[Na+].[CH2:3](Br)[CH2:4][CH2:5][CH3:6].[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C@:16]([OH:25])([CH2:23][SH:24])[CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[ClH:26]>CO.C(OCC)C>[CH2:3]([S:24][CH2:23][C@:16]([C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[Cl:8])([OH:25])[CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)[CH2:4][CH2:5][CH3:6].[ClH:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 13420610(R)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-mercapto-2-propanol

Product 2

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of sodium hydroxide (2 g) in methanol (100 ml) were added n-butylbromide (2 g) and (R)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-3-mercapto-2-propanol (II) obtained in Example 2 at a temperature of 20°-25° C. in nitrogen atmosphere. The mixture was stirred at 25°-30° C. for 5 hours and then concentrated under reduced pressure. The residue was treated with water (50 ml) and extracted with dichloromethane (50 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was dissolved in diethyl ether (20 ml), and hydrogen chloride gas was introduced thereto. Precipitated crystals were collected by filtration and dried to give (R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (I: n=3) hydrochloride (3.4 g). Yield, 86.8%. M.P., 168°-169° C. [α]D20 -89.7° (c=1, methanol). The optical purity of the product was not less than 99% determined by high performance liquid chromatography.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with water (50 ml)
  3. extractionextracted with dichloromethane (50 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customPrecipitated crystals
  9. filtrationwere collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-1c8a6773b4544a1c9e65f33ca6ff3f00
Source dataset
uspto-grants-1985_07
Patent number
US04526983

Reaction notes

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