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

HRID 65025
Notes
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Reaction equation

HRID 65025 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[C:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])([OH:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:4][CH:3]=1.[C:26](Cl)(=O)[O:27]C1C=CC=CC=1.C(=O)([O-])O.[Na+].C(Cl)Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:25][C:26](=[O:27])[O:16][C:9]2([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 13777825HCID 13777825, compound

Product 1

HCID 137270005-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-oxo-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolaneYield 87.5%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

To a solution of 500 mg of 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-1,2-propanediol in 1 ml of dry pyridine is added 300 mg of phenyl chlorocarbonate, and the resultant mixture is allowed to react at room temperature for 18 hours. The reaction mixture is mixed with aqueous sodium hydrogencarbonate solution and shaken with methylene chloride. The organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica-gel, which is eluted with 2% methanolmethylene chloride. The eluate is concentrated and the residue is crystallized from ethyl acetate-isopropyl ether to give 466 mg of 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-2-oxo-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolane as crystals melting at 178° to 179° C. The yield is 87%.

Workup

  1. customto react at room temperature for 18 hours
  2. washThe organic layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica-gel, which
  6. washis eluted with 2% methanolmethylene chloride
  7. concentrationThe eluate is concentrated
  8. customthe residue is crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-032c252c1d5a4fc1aa0d031bd1dc3929
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04612322

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes