Trifluoroacetic acid → HCID 178456703, compound
Reaction equation
C([S:14][C:15]1[N:16]=[N:17][N:18]([CH2:20][C:21]#[CH:22])[N:19]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:20]([N:18]1[N:17]=[N:16][C:15]([SH:14])=[N:19]1)[C:21]#[CH:22]Participants
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 5-benzhydrylthio-2-(2-propynyl)-2H-tetrazole (1.05 g), anisole (1.79 g) and trifluoroacetic acid (9.7 ml) was stirred at 22° C. for 1.5 hours, at 35° C. for an hour, at 50° C. for 1.7 hours and then at room temperature for a further 14 hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate (10 ml) and the mixture was adjusted to pH 8.5 with 2 N aqueous solution of sodium hydroxide. The aqueous layer was separated, washed with ethyl acetate (20 ml×2) and thereto was added ethyl acetate. The resulting mixture was adjusted to pH 2.5 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated to give an oil of 2-(2-propynyl)-2H-tetrazole-5-thiol (0.3 g).
Workup
- waitat room temperature for a further 14 hours
- filtrationThe reaction mixture was filtered
- customthe filtrate was evaporated under reduced pressure
- additionTo the residue was added a saturated aqueous solution of sodium bicarbonate (10 ml)
- customThe aqueous layer was separated
- washwashed with ethyl acetate (20 ml×2)
- additionwas added ethyl acetate
- customThe ethyl acetate layer was separated
- washwashed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-dddc4b24a9654595816dc509a79479fd
- Source dataset
- uspto-grants-1983_09
- Patent number
- US04405617
Reaction notes
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