Imidazole → HCID 57106152, compound

HRID 649613Notes

Reaction equation

HRID 649613 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.[CH2:10]([S:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27])=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[OH:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:19]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[CH:18][S:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 14100235HCID 14100235, compound

Product 1

HCID 57106152HCID 57106152, 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. After stirring the reaction mixture for 30 minutes, 2.58 g of 2-benzylthio-2'-hydroxyacetophenone was added, followed by further stirring at room temperature for 2 hours. Ice water was added to the reaction mixture, followed by 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 and was then subjected to chromatography on a silica gel column. Upon concentration of the resultant eluate, there were obtained 180 mg of Isomer A (m.p. 196°-198° C.; Compound 1) and 1.0 g of Isomer B (m.p. 136.5°-138° C.; Compound 2) of 1-(2-hydroxyphenyl)-1-imidazolyl-2-benzylthioethylene (in formula (I), R1, R2, R3 =H, R4 =--SCH2C6H5), both, as colorless crystals.

Workup

  1. additionwas added with ice-
  2. temperaturecooling
  3. stirringby further stirring at room temperature for 2 hours
  4. extractionfollowed by 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-45870dc4ab8749cd80491062cca3dff3
Source dataset
uspto-grants-1988_04
Patent number
US04740601

Reaction notes

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