Water → 1-[[2-(4-methoxyphenyl)-1,3-oxathiolan-2-yl]methyl]-1H-1,2,4-triazole

HRID 2248236

Reaction equation

HRID 2248236 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1.[SH:17][CH2:18][CH2:19]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(O)CCC.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:10][N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[S:17][CH2:18][CH2:19][O:16]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 138160051-(4-Methoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Product 1

HCID 194304951-[[2-(4-methoxyphenyl)-1,3-oxathiolan-2-yl]methyl]-1H-1,2,4-triazoleYield 15.7%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 32.5 g 1- (4-methoxyphenyl)-2-(1H-1,2,4-triazole-1-yl) ethanone in 500 ml dry toluene and 250 ml 1-butanol was added 23.4 g 2-mercaptoethanol and 38.0 g p-toluenesulfonic acid. The thickened slurry was refluxed under a Dean-Stark trap for about 40 hours, until no more water collected. The solvent was evaporated leaving a solid residue which was dissolved in dichloromethane and washed twice with 10% aqueous sodium hydroxide and once with water. The organic layer was dried, filtered and evaporated to leave an oily residue which partially solidified on high vacuum pumping. The residue was triturated with hot toluene/cyclohexane, cooled and filtered to give 6.5 g of product.

Workup

  1. customcollected
  2. customThe solvent was evaporated
  3. customleaving a solid residue which
  4. washwashed twice with 10% aqueous sodium hydroxide and once with water
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave an oily residue which
  9. customThe residue was triturated with hot toluene/cyclohexane
  10. temperaturecooled
  11. filtrationfiltered

Sources & evidence

ORD record
ord-62c432f2baed422e9afc345bfbdefe6a
Source dataset
uspto-grants-1991_08
Patent number
US05039332

Linked notes

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