Trifluoroacetic acid → HCID 178456704, compound
Reaction equation
C([S:14][C:15]1[N:19]([CH2:20][C:21]#[CH:22])[N:18]=[N:17][N:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:20]([N:19]1[C:15]([SH:14])=[N:16][N:17]=[N:18]1)[C:21]#[CH:22]Participants
Conditions
- Temperature
- 20 °C
Procedure
A mixture of 5-benzhydrylthio-1-(2-propynyl)-1H-tetrazole (0.35 g), anisole (0.6 g) and trifluoroacetic acid (3.4 ml) was stirred for 30 minutes at 20° C. and then allowed to stand for 45 minutes. The reaction mixture was filtered and the filter cake was washed with isopropyl ether. The filtrate and the washing were combined and evaporated under reduced pressure. After the addition of the residue to a saturated aqueous solution of sodium bicarbonate precooled to 10° C., the resulting mixture was adjusted to pH 8.5 with 2N aqueous solution of sodium hydroxide and washed with ethyl acetate. The washed aqueous layer was adjusted to pH 2.5 with 10% hydrochloric acid under ice-cooling and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 1-(2-propynyl)-1H-tetrazole-5-thiol (95 mg), which is decomposed from 60° to 71° C.
Workup
- waitto stand for 45 minutes
- filtrationThe reaction mixture was filtered
- washthe filter cake was washed with isopropyl ether
- customevaporated under reduced pressure
- additionAfter the addition of the residue to a saturated aqueous solution of sodium bicarbonate
- customprecooled to 10° C.
- washwashed with ethyl acetate
- temperaturecooling
- extractionextracted with ethyl acetate
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-4fa4a12ea36e4a57a1fcaac1b366fc64
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04533738
Reaction notes
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