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 2N 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-61bac776d79a49158fecb2c88836b891
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04563450
Reaction notes
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