Imidazole → HCID 22821713, compound

HRID 1388507Notes

Reaction equation

HRID 1388507 reaction equation
Br[CH:2]1[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[S:4][CH2:3]1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(#N)C>O>[Cl:13][C:7]1[CH:8]=[CH:9][C:10]2[C@H:11]([OH:12])[C@H:2]([CH2:3][C:15]3[NH:14][CH:18]=[CH:17][N:16]=3)[S:4][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6342AcetonitrileHCID 13059709HCID 13059709, compound

Product 1

HCID 22821713HCID 22821713, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 3-bromo-7-chlorothiochroman-4-ol (5.27 gms., 18.8 mmols) and imidazole (12.8 gms., 188 mmols) to acetonitrile (100 ml.), and heat at reflux temperature for 4 hours. Pour the reaction mixture into water (500 ml.), and extract with chloroform (500 ml.). Wash the organic layer with water (500 ml.), dry the organic layer over anhydrous magnesium sulfate, filter and evaporate in vacuo. Triturate the resultant resultant residue with anhydrous ether, filter and recrystallize from acetonitrile to give cis-6-chloro-2,3-dihydro-3-hydroxy-2-(1'-imidazolylmethyl)benzo(b)thiophene.

Workup

  1. temperatureheat
  2. temperatureat reflux temperature for 4 hours
  3. extractionextract with chloroform (500 ml.)
  4. washWash the organic layer with water (500 ml.)
  5. dry with materialdry the organic layer over anhydrous magnesium sulfate
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customTriturate the resultant resultant residue with anhydrous ether
  9. filtrationfilter
  10. customrecrystallize from acetonitrile

Sources & evidence

ORD record
ord-396df2522f7e4cb28996cba9c7fa1731
Source dataset
uspto-grants-1984_02
Patent number
US04431816

Reaction notes

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