p-Toluenesulfonic acid → HCID 14723983, compound

HRID 1199214Notes

Reaction equation

HRID 1199214 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])(O)[CH2:9][C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)=[C:4]([CH3:25])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])=[CH:9][C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)=[C:4]([CH3:25])[CH:3]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14723982HCID 14723982, compound

Product 1

HCID 14723983HCID 14723983, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1,1-bis-(4-fluoro-2-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol (0.5 g, 1.5 mmoles) and p-toluenesulfonic acid (0.2 g) was heated at reflux in toluene (30 mL) for 16 hours. The mixture was cooled, diluted with diethyl ether (50 mL) and extracted with saturated sodium bicarbonate solution and water. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was triturated with diethyl ether to give 0.3 g of the title compound; m.p.=120°-125° C.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. extractionextracted with saturated sodium bicarbonate solution and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-39a63e28f6dd420b8895433f05ca3bb4
Source dataset
uspto-grants-1990_02
Patent number
US04898949

Reaction notes

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