Imidazole → HCID 57167807, compound

HRID 649614Notes

Reaction equation

HRID 649614 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.C(N(CC)CC)C>[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

6

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 20141947HCID 20141947, compound

Product 1

HCID 57167807HCID 57167807, 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 resulting mixture was stirred for 30 minutes, followed by addition of 2.42 g of 2-n-propylthio-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 19; m.p. 191°-192° C.) and 1.1 g of Isomer B (Compund 18; m.p. 127°-128° C.) of 1-(2-hydroxyphenyl)-1 -imidazolyl-2-n-propylthioethylene were obtained respectively as colorless crystals.

Workup

  1. additionwas added with ice-
  2. temperaturecooling
  3. stirringThe reaction mixture was stirred at room temperature for further 2 hours
  4. extractionfollowed by its extraction with methylene chloride
  5. washThe organic, i.e., methylene chloride layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in chloroform

Sources & evidence

ORD record
ord-39e3801d15d34153908b14e50a50c0cd
Source dataset
uspto-grants-1988_04
Patent number
US04740601

Reaction notes

Loading…