Ammonia → 2-(2,4-Dichlorophenyl)-3-(1H-imidazol-1-yl)propane-1,2-diol

HRID 1462858Notes

Reaction equation

HRID 1462858 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH2:11][O:10]1.S(=O)(=O)(O)[OH:19].N>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:19])([CH2:11][OH:10])[CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 2783908AG-H-13688

Product 1

HCID 133368182-(2,4-Dichlorophenyl)-3-(1H-imidazol-1-yl)propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2,4-dichlorophenyl)-2-(imidazol-1-yl)methyloxirane (170.4 g; Japanese Patent Publications (unexamined) Nos. 12372/1981 and 106666/1982) and a 25% aqueous sulfuric acid solution (1193 g) was stirred at 80°-85° C. for 5 hours. To the reaction mixture, ethyl acetate (405 ml) and a 28% aqueous ammonia solution (520 ml) were added dropwise at 0°-10° C., and then the mixture was stirred for 1 hour at the same temperature. The resulting precipitate was collected by filtration and dried at 80° C. (10 mmHg) for 5 hours to give 2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2,3-propanediol. Yield, 146 g; 80.3%. M.P., 123.5°-124.5° C.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried at 80° C. (10 mmHg) for 5 hours

Sources & evidence

ORD record
ord-97637ad880164aee9de9251c52446f04
Source dataset
uspto-grants-1984_07
Patent number
US04461774

Reaction notes

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