Chloroform → 4-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-2-oxo-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolane

HRID 65021Notes

Reaction equation

HRID 65021 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[OH:11].[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27].C(Cl)(Cl)Cl>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH:10]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[O:11][C:26](=[O:27])[O:25]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 682631,1'-CarbonyldiimidazoleHCID 13391691HCID 13391691, compound

Product 1

HCID 134227404-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-2-oxo-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolaneYield 78.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 500 mg of 2-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-1,2-propanediol, 530 mg of 1,1'-carbonyldiimidazole and 10 ml of dry chloroform is heated under reflux for 1 hour. Water is added to the reaction mixture, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated. The residue is chromatographed on a column of silica-gel and eluted with a mixture of methylene chloride and methanol (100:0-98:2 v/v). The eluate is concentrated, and the residue is crystallized from ethyl acetate-isopropyl ether to give 420 mg of 4-(2,4-dichlorophenyl)-5-(4-fluorophenyl)-2-oxo-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolane as crystals. m.p. 191°-192° C. Yield: 78.7%

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. customthe chloroform layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica-gel
  7. washeluted with a mixture of methylene chloride and methanol (100:0-98:2 v/v)
  8. concentrationThe eluate is concentrated
  9. customthe residue is crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-d9d88c7f165b4092b8a11ac01e3781f1
Source dataset
uspto-grants-1986_09
Patent number
US04612322

Reaction notes

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