Imidazole → HCID 23350201, compound

HRID 2058317Notes

Reaction equation

HRID 2058317 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])=[CH:16][C:15]=1[Cl:21].O>CO.CN(C)C=O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[NH:13][CH2:12][CH:11]([OH:22])[CH2:10][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 10942334Sodium MethoxideHCID 233502121-Chloro-3-(2,4-dichloroanilino)propan-2-ol

Product 1

HCID 23350201HCID 23350201, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

108 Grams (1.586 mol) of imidazole and 283 g (1.574 mol) of sodiummethylate solution 30% in methanol are mixed and the solution is then concentrated to dryness under reduced pressure at 50° C. The crystalline residue is dissolved in 400 ml dimethylformamide at 110° C. A solution of 259 g (1.017 mol) of N-(3-chloro-2-hydroxypropyl)-2,4-dichloroaniline in 500 ml of dimethylformamide is added dropwise at 110° C. within 30 minutes. Upon completion the reaction mixture is refluxed for 2 hours and then cooled down. The solution is now added dropwise to 3400 ml of water at room temperature within 30 minutes and stirred for another hour. The precipitated granular substance is filtered off, washed with water and dried in vacuum at 50° C. to yield 263.5 g 1-[3-(2,4-dichloroanilino)-2-hydroxypropyl]-imidazole, M.P. 107°-109° C.

Workup

  1. concentrationthe solution is then concentrated to dryness under reduced pressure at 50° C
  2. dissolutionThe crystalline residue is dissolved in 400 ml dimethylformamide at 110° C
  3. temperatureUpon completion the reaction mixture is refluxed for 2 hours
  4. temperaturecooled down
  5. filtrationThe precipitated granular substance is filtered off
  6. washwashed with water
  7. customdried in vacuum at 50° C.

Sources & evidence

ORD record
ord-34c61eae9de941fdbed0e003dc3b090d
Source dataset
uspto-grants-1980_07
Patent number
US04215220

Reaction notes

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