Imidazole → HCID 20303078, compound

HRID 1732884Notes

Reaction equation

HRID 1732884 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C[O-].[Na+].[Cl:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:23]([OH:34])([CH2:32]Cl)[CH2:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)=[CH:18][C:19]=3[CH2:20]2)=[CH:12][CH:11]=1.O>CO.CN(C)C=O>[Cl:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:23]([OH:34])([CH2:32][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[CH2:24][C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=4)=[CH:18][C:19]=3[CH2:20]2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 10942334Sodium MethoxideHCID 20303085HCID 20303085, compound

Product 1

HCID 20303078HCID 20303078, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

9 g (0.12 mol) of imidazole are added to a solution of 4.2 g (0.078 mols) of sodium methylate in 22 ml of methanol; a solution of 2-(7-chlorofluoren-2-yl)-3-chloro-1-(4-chlorophenyl)-propan-2-ol in 45 ml of dimethylformamide is then added dropwise and the mixture is warmed to 60° C. for 90 minutes. The mixture is poured into 2,000 ml of water, the crystalline mass which has separated out is dissolved in methylene chloride, the solution is washed with water, dried over sodium sulphate and filtered and the filtrate is concentrated in vacuo. The residue is made to crystallise by stirring with diethyl ether; the crystals are stirred with a little methyl alcohol and filtered off. 16.2 g (62.5% of theory) of 2-(7-chlorofluoren-2-yl)-1-(4-chlorophenyl)-3-(imidazol-1-yl)-propan-2-ol of melting point 218° C. are obtained.

Workup

  1. customthe crystalline mass which has separated out
  2. dissolutionis dissolved in methylene chloride
  3. washthe solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customto crystallise
  8. stirringthe crystals are stirred with a little methyl alcohol
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-0ff15faca133447c8f2000bb87a8a020
Source dataset
uspto-grants-1980_12
Patent number
US04239765

Reaction notes

Loading…