Nitric Acid → 1-[p-(difluoromethylsulfinyl)phenyl]-1H-tetrazole

HRID 596156Notes

Reaction equation

HRID 596156 reaction equation
[F:1][CH:2]([F:15])[S:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[CH:6][CH:5]=1.S(=O)(=O)(O)[OH:17].[N+]([O-])(O)=O>>[F:15][CH:2]([F:1])[S:3]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[CH:6][CH:5]=1)=[O:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 214509701-{4-[(Difluoromethyl)sulfanyl]phenyl}-1H-tetrazole

Product 1

HCID 214509671-[p-(difluoromethylsulfinyl)phenyl]-1H-tetrazole

Procedure

1-[p-(Difluoromethylthio)phenyl]-1H-tetrazole (1.0 gram) was added to a cold mixture of 5 ml. of concentrated sulfuric acid and 5 ml. of concentrated nitric acid and stirred for 40 minutes in the cold, then for 40 minutes at room temperature. The reaction mixture was poured onto ice and extracted with ethyl acetate. The ethyl acetate solution was extracted with water, dried over magnesium sulfate, and evaporated to afford an oil which was crystallized from ethyl acetate-hexane. Two recrystallizations from the same solvents gave 143 mg. of product, m.p. 109°-112° C.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate solution was extracted with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto afford an oil which
  7. customwas crystallized from ethyl acetate-hexane
  8. customTwo recrystallizations from the same solvents
  9. customgave 143 mg

Sources & evidence

ORD record
ord-00c96ba8e59b49e0bb0083a60e1e0cd7
Source dataset
uspto-grants-1977_03
Patent number
US04010179

Reaction notes

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