Imidazole → 1-[3-(3,4-Dichloroanilino)-2-hydroxypropyl]imidazole

HRID 2058318Notes

Reaction equation

HRID 2058318 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C[O-].[Na+].Cl[CH2:10][CH:11]([OH:22])[CH2:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1.O>CN(C)C=O>[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[Cl:20])[NH:13][CH2:12][CH:11]([OH:22])[CH2:10][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 10942334Sodium MethoxideHCID 23350203N-(3-chloro-2-hydroxypropyl)-3,4-dichloroaniline

Product 1

HCID 233502001-[3-(3,4-Dichloroanilino)-2-hydroxypropyl]imidazoleYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

19.9 Grams (0.293 mol) of imidazole and 54.7 g (0.304 mol) of sodium methylate solution (30% in methanol) are mixed and concentrated to dryness at 50° C./12 Torr. 80 Ml of dimethylformamide are added to the thus-formed imidazole sodium salt. The mixture is heated to 110° C. and a solution of 50 g (0.197 mol) of N-(3-chloro-2-hydroxypropyl)-3,4-dichloroaniline in 100 ml of dimethylformamide is added dropwise at this temperature over a period of 30 minutes. This addition finished, the reaction solution is further heated and refluxed for 2 hours. The solution is then cooled to 90° C. and 650 ml of water are added. The reaction mixture is left standing for 12 hours. The solid precipitant is filtered off, washed with water and dried at 50° C./12 Torr. For purification the substance is recrystallized under filtration with active charcoal from 100 ml ethyl acetate to yield 22 g of 1-[3-(3,4-dichloroanilino)-2-hydroxypropyl]-imidazole, M.P. 98°-100° C.

Workup

  1. concentrationconcentrated to dryness at 50° C./12 Torr
  2. addition80 Ml of dimethylformamide are added to the thus-formed imidazole sodium salt
  3. additionThis addition
  4. temperaturethe reaction solution is further heated
  5. temperaturerefluxed for 2 hours
  6. temperatureThe solution is then cooled to 90° C.
  7. waitThe reaction mixture is left
  8. filtrationThe solid precipitant is filtered off
  9. washwashed with water
  10. customdried at 50° C./12 Torr
  11. customFor purification the substance
  12. customis recrystallized under filtration with active charcoal from 100 ml ethyl acetate

Sources & evidence

ORD record
ord-8ea916716e0740e4bc8a3786ae7beae7
Source dataset
uspto-grants-1980_07
Patent number
US04215220

Reaction notes

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