Imidazole → HCID 20523185, compound

HRID 223172Notes

Reaction equation

HRID 223172 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:22])[CH:13]([CH2:18]N(C)C)[CH2:14][S:15]2)=[CH:10][CH:9]=1>O>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:22])[CH:13]([CH2:18][C:2]3[NH:1][CH:5]=[CH:4][N:3]=3)[CH2:14][S:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 20448226HCID 20448226, compound

Product 1

HCID 20523185HCID 20523185, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve imidazole (25.8 gms., 380 mmols) in water (100 ml.) and add 7-chloro-3-(dimethylaminomethyl)thiochroman-4-one hydrochloride (11.1 gms., 38.0 mmols). Stir the reaction mixture overnight at room temperature, then add water (1 liter) and extract with chloroform (500 ml.). Wash the chloroform solution with 2 liter portions of water, dry over anhydrous magnesium sulfate, filter and evaporate in vacuo to a residue. Chromatograph the residue on a silica gel column eluting with chloroform. Combine the like eluates as determined by thin layer chromatography and evaporate in vacuo to a residue comprising 7-chloro-3-(1'-imidazolylmethyl)thiochroman-4-one. Further purify by recrystallization from chloroform/hexane, m.p. 104°-105° C.

Workup

  1. extractionadd water (1 liter) and extract with chloroform (500 ml.)
  2. washWash the chloroform solution with 2 liter portions of water
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. customevaporate in vacuo to a residue
  6. washChromatograph the residue on a silica gel column eluting with chloroform
  7. customevaporate in vacuo to a residue comprising 7-chloro-3-(1'-imidazolylmethyl)thiochroman-4-one
  8. customFurther purify by recrystallization from chloroform/hexane, m.p. 104°-105° C.

Sources & evidence

ORD record
ord-81bc539a5ef84d62bfc476a9c9719be7
Source dataset
uspto-grants-1982_10
Patent number
US04352808

Reaction notes

Loading…