Butyl bromide → Hydrochloric Acid

HRID 370557Notes

Reaction equation

HRID 370557 reaction equation
[Cl:1]C1C=C[C:5]([C@H:8](C(C)C)[C:9]([S:11][CH2:12][C@:13]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])([OH:20])[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=O)=[CH:4]C=1.[OH-].[K+].C(Br)CCC>CO>[CH2:9]([S:11][CH2:12][C@:13]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])([OH:20])[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[CH2:8][CH2:5][CH3:4].[ClH:1]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 13420608(R)-3-[(S)-2-(4-chlorophenyl)isovalerylthio]-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol

Product 2

HCID 313Hydrochloric AcidYield 601.4%HCID 13420611(R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of (R)-3-[(S)-2-(4-chlorophenyl)isovalerylthio]-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (VIb) (49.5 g) obtained in Example 1 in methanol (500 ml) were added a 10% methanolic potassium hydroxide solution (240 g) and n-butylbromide (21.6 g) at -5° to 0° C. in nitrogen atmosphere. The slurry was stirred at the same temperature for 2 hours and then at 30° C. for 3 hours. Methanol was removed by distillation under atmospheric pressure, and the residue was treated with water (200 ml) and extracted with 1,2-dichloroethane (200 ml). The extract was washed successively with water and 12% hydrochloric acid (200 ml) and concentrated in vacuo. To the residue were added toluene (100 ml) and methyl ethyl ketone (35 ml), and the slurry was stirred at 15° C. for 3 hours. Filtration and drying in vacuo gave a crude product (25.7 g), which was recrystallized from methyl ethyl ketone to give (R)-3-(n-butylthio)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (I: n=3) hydrochloride (21.8 g) as colorless needles. Yield, 55%. M.P., 168.5°-170° C. [α]D20 -89.8° (c=1, methanol).

Workup

  1. waitat 30° C. for 3 hours
  2. customMethanol was removed by distillation under atmospheric pressure
  3. additionthe residue was treated with water (200 ml)
  4. extractionextracted with 1,2-dichloroethane (200 ml)
  5. washThe extract was washed successively with water and 12% hydrochloric acid (200 ml)
  6. concentrationconcentrated in vacuo
  7. additionTo the residue were added toluene (100 ml) and methyl ethyl ketone (35 ml)
  8. stirringthe slurry was stirred at 15° C. for 3 hours
  9. filtrationFiltration
  10. customdrying in vacuo
  11. customgave a crude product (25.7 g), which
  12. customwas recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-d4129998c40a4fb3a91a9dc847b95a34
Source dataset
uspto-grants-1985_07
Patent number
US04526983

Reaction notes

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