HCID 178440853, compound → HCID 178440601, compound

HRID 428607Notes

Reaction equation

HRID 428607 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CS(O)(=O)=O>[C:1]([C:5]1[CH:10]=[C:9]2[C:8]([CH2:11][CH2:12][CH:13]2[C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 178440853HCID 178440853, compound

Product 1

HCID 178440601HCID 178440601, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(4-tert-butylphenyl)-1-(1H-imidazol-4-yl)-propan-1-ol (2.0 g) and methanesulfonic acid (30 ml) is heated at 60° C. for 5 minutes. The reaction is then quenched by pouring it into ice-water solution. The acidic solution is made basic with ammmonium hydroxide solution, and extracted with ethyl acetate. The combined organic layers are washed with water, dried with sodium sulfate, and evaporated to dryness under reduced pressure. The crude product is purified by flash chromatography by eluting with methylene chloride-methanol as eluent. The product is crystallized from ethyl acetate. The yield is 220 mg.

Workup

  1. customThe reaction is then quenched
  2. additionby pouring it into ice-water solution
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers are washed with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe crude product is purified by flash chromatography
  8. washby eluting with methylene chloride-methanol as eluent
  9. customThe product is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-77278b3e8b7f443f8c1f2738908baa37
Source dataset
uspto-grants-2001_11
Patent number
US06313311B1

Reaction notes

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