p-Toluenesulfonic acid → HCID 14723983, compound

HRID 974484Notes

Reaction equation

HRID 974484 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-1003e3e2cdf9483f9b36fd567008b46e
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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