2-Mercaptoethanol → 1-{[2-([1,1'-Biphenyl]-4-yl)-1,3-oxathiolan-2-yl]methyl}-1H-1,2,4-triazole

HRID 1608262Notes

Reaction equation

HRID 1608262 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:14])[CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:3][CH:2]=1.[SH:21][CH2:22][CH2:23]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(O)CCC>[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][C:4]([C:7]2([CH2:8][N:9]3[CH:13]=[N:12][CH:11]=[N:10]3)[S:21][CH2:22][CH2:23][O:14]2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 136031961-([1,1'-Biphenyl]-4-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Product 1

HCID 146963411-{[2-([1,1'-Biphenyl]-4-yl)-1,3-oxathiolan-2-yl]methyl}-1H-1,2,4-triazoleYield 41.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 1140TolueneSolvent

Procedure

To a slurry of 13.1 g of 1-[1,1'biphenyl]-4-yl-2-(1H-1,2,4-triazol-1-yl)ethanone in 175 ml dry toluene and 70 ml 1-butanol was added, with stirring, 7.8 g 2-mercaptoethanol and 12.3 g p-toluenesulfonic acid. The resultant thickened slurry was refluxed under a Dean-Stark [trademark] trap for 72 hours. At this point, no further water was collected. After the reaction was allowed to cool, the solid was filtered out, slurried in dichloromethane and shaken with 10% aqueous sodium hydroxide and once with water. The organic layer was dried and evaporated to leave an oil which solidified on high-vacuum pumping. This solid was triturated with petroleum ether to give 6.7 g of 1-[(2-[1,1'-biphenyl]-4-yl-1,3-oxathiolan-2-yl)methyl]-1H-1,2,4-triazole, the product of this reaction. The melting point of this compound was 85°-90° C.

Workup

  1. temperaturewas refluxed under a Dean-Stark [trademark] trap for 72 hours
  2. customAt this point, no further water was collected
  3. temperatureto cool
  4. filtrationthe solid was filtered out
  5. stirringshaken with 10% aqueous sodium hydroxide and once with water
  6. customThe organic layer was dried
  7. customevaporated
  8. customto leave an oil which
  9. customThis solid was triturated with petroleum ether

Sources & evidence

ORD record
ord-5f23e669dd034bb9bbaa43c94a91ed70
Source dataset
uspto-grants-1989_09
Patent number
US04870094

Reaction notes

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