Imidazole → HCID 57323911, compound

HRID 649617Notes

Reaction equation

HRID 649617 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.C(N(CC)CC)C>[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

6

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 12227422HCID 12227422, compound

Product 1

HCID 57323911HCID 57323911, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

To a suspension of 1.02 g of imidazole, 1.52 g of triethylamine 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 addition of 2.44 g of 2-phenylthio-2'-hydroxyacetophenone and a solution consisting of 1.16 g of triethylamine and 5 ml of dry methylene chloride. The reaction mixture was stirred at room temperature for further 2 hours. Ice water was then added to the reaction mixture, followed by its extraction with methylene chloride. The organic, i.e., methylene chloride layer was washed with water, dried over magnesium sulfate, and then concentrated. The residue was dissolved in chloroform. The chloroform solution was subjected to chromatography on a silica gel column. Upon concentration of the resulting eluate, 0.2 g of Isomer A (Compound 61; m.p. 235.5°-237° C.) and 0.9 g of Isomer B (Compound 62; m.p. 152.5°-154° C.) of 1-(2-hydroxyphenyl)-1 -imidazolyl-2-phenylthioethylene were obtained respectively as colorless crystals.

Workup

  1. additionwas added with ice-
  2. temperaturecooling
  3. extractionfollowed by its extraction with methylene chloride
  4. washThe organic, i.e., methylene chloride layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in chloroform

Sources & evidence

ORD record
ord-852034abbb2d473b8fca54559b680349
Source dataset
uspto-grants-1988_04
Patent number
US04740601

Reaction notes

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