Imidazole → HCID 57167807, compound

HRID 649615Notes

Reaction equation

HRID 649615 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.[CH2:10]([S:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=O)[CH2:11][CH3:12]>C(Cl)Cl>[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[CH:14][S:13][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 20141947HCID 20141947, compound

Product 1

HCID 57167807HCID 57167807, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4.08 g of imidazole and 30 ml of dry methylene chloride, 1.78 g of thionyl chloride was added with ice-cooling. The resultant mixture was stirred for 30 minutes, followed by an addition of 2.10 g of 2-n-propylthio-2'-hydroxyacetophenone. The thus-obtained mixture was stirred at room temperature for 2 hours. Ice water was then added to the reaction mixture, followed by its extraction with methylene chloride. The methylene chloride extract was then subjected to a post treatment in the same manner as in Example 5. The reaction product was separated by column chromatography, thereby obtaining 0.2 g of Isomer A (Compound 18) and 1.0 g of Isomer B (Compound 19) of 1-(2-hydroxyphenyl)-1-imidazolyl-2-n-propylthioethylene as colorless crystals respectively.

Workup

  1. additionwas added with ice-
  2. temperaturecooling
  3. extractionfollowed by its extraction with methylene chloride
  4. extractionThe methylene chloride extract
  5. customThe reaction product was separated by column chromatography

Sources & evidence

ORD record
ord-3567843d968144ee87f23985edb3e174
Source dataset
uspto-grants-1988_04
Patent number
US04740601

Reaction notes

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