Imidazole → HCID 53749427, compound

HRID 569015Notes

Reaction equation

HRID 569015 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][N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)[S:4][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6342AcetonitrileHCID 13059709HCID 13059709, compound

Product 1

HCID 53749427HCID 53749427, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 3-bromo-7-chlorothiochroman-4-ol (5.27 g., 18.8 mmole) and imidazole (12.8 g., 188 mmole) to acetonitrile (100 mL.), and reflux 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 it over anhydrous magnesium sulfate, filter and evaporate in vacuo. Triturate the residue with anhydrous ether, filter and recrystallize from acetonitrile to give (±)-cis-6-chloro-2,3-dihydro-3-hydroxy-2-(1H-1-imidazolylmethyl)benzo[b]thiophene, m.p. 164°-165° C.

Workup

  1. temperaturereflux for 4 hours
  2. extractionextract with chloroform (500 mL.)
  3. washWash the organic layer with water (500 mL.)
  4. dry with materialdry it over anhydrous magnesium sulfate
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customTriturate the residue with anhydrous ether
  8. filtrationfilter
  9. customrecrystallize from acetonitrile

Sources & evidence

ORD record
ord-7d676c9c320b4482afa164061ddc8a0c
Source dataset
uspto-grants-1988_03
Patent number
US04731364

Reaction notes

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