Ethyl orthoformate → 1-{4-[(Difluoromethyl)sulfanyl]phenyl}-1H-tetrazole
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customevaporated at reduced pressure
- additionThe residue was diluted with water
- filtrationfiltered
- customdried
- customrecrystallized from ethyl acetate
- 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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