Ethyl orthoformate → 1-{4-[(Difluoromethyl)sulfanyl]phenyl}-1H-tetrazole

HRID 596155Notes

Reaction equation

HRID 596155 reaction equation
[F:1][CH:2]([F:11])[S:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[N-:12]=[N+:13]=[N-:14].[Na+].[CH:16](OCC)(OCC)OCC>C(O)(=O)C>[F:11][CH:2]([F:1])[S:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH:16]=[N:14][N:13]=[N:12]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 36891354-((Difluoromethyl)sulfanyl)aniline

Product 1

HCID 214509701-{4-[(Difluoromethyl)sulfanyl]phenyl}-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of p-(difluoromethylthio)aniline (4.0 g.), sodium azide (4.0 g.), triethyl orthoformate (25 ml.), and acetic acid (25 ml.) was heated at 95° C. for 4.5 hours and then evaporated at reduced pressure. The residue was diluted with water, filtered, dried and recrystallized from ethyl acetate:hexane to give crystals, m.p. 94°-97° C.

Workup

  1. customevaporated at reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationfiltered
  4. customdried
  5. customrecrystallized from ethyl acetate
  6. customhexane to give crystals, m.p. 94°-97° C.

Sources & evidence

ORD record
ord-83a6de1f5ab84ff1b31d983b88ac5289
Source dataset
uspto-grants-1977_03
Patent number
US04010179

Reaction notes

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