Methanesulfonic Acid → HCID 178420078, compound

HRID 1935748Notes

Reaction equation

HRID 1935748 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH:7](O)[CH2:8][CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:4]=[CH:3]1.CS(O)(=O)=O.[OH-].[Na+]>O>[C:11]1([CH:10]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:7]([C:5]3[N:4]=[CH:3][NH:2][CH:6]=3)[CH2:8][CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 178479685HCID 178479685, compound

Product 1

HCID 178420078HCID 178420078, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(1H-imidazol-4-yl)-4,4-diphenylbutan-1-ol hydrochloride (2.0 g) and methanesulfonic acid (40 ml) was heated at 100° C. for 40 minutes. The cooled reaction mixture was poured into water and was made alkaline with sodium hydroxide solution. The product was extracted into ethyl acetate, which was washed with water, dried with sodium sulfate and evaporated under reduced pressure to give a crude product of racemic cis and trans diastereomers. The product was purified by flash chromatography (elution with a dichloromethane—methanol gradient). The base product was dissolved in ethyl acetate and converted to its hydrochloride salt with hydrogen chloride gas.

Workup

  1. customThe cooled reaction mixture
  2. extractionThe product was extracted into ethyl acetate, which
  3. washwas washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-55c9151904b94131abe3c239254677d2
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

Loading…