Imidazole → HCID 57323911, compound

HRID 649618Notes

Reaction equation

HRID 649618 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.[C:10]1([S:16][CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[OH:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[CH:17][S:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 12227422HCID 12227422, compound

Product 1

HCID 57323911HCID 57323911, 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-phenylthio-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 10. The reaction product was separated by column chromatography, thereby obtaining 0.2 g of Isomer A (Compound 61) and 1.0 g of Isomer B (Compound 62) of 1-(2-hydroxyphenyl)-1-imidazolyl-2-phenylthioethylene 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-5351f6c57b014a2c88e6dc17e0619fbb
Source dataset
uspto-grants-1988_04
Patent number
US04740601

Reaction notes

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