Hydrochloric Acid → 4-Mercapto-1-Methyl-tetrahydrothiopyraniumtriflate

HRID 978602Notes

Reaction equation

HRID 978602 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].C([S:12][CH:13]1[CH2:18][CH2:17][S+:16]([CH3:19])[CH2:15][CH2:14]1)(=O)C.[OH-].[Na+].Cl>O>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[SH:12][CH:13]1[CH2:18][CH2:17][S+:16]([CH3:19])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867414894-Acetylthio-1-methyl-tetrahydrothiopyraniumtriflate

Product 1

HCID 867414874-Mercapto-1-Methyl-tetrahydrothiopyraniumtriflate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (5° C.) solution of 4-acetylthio-1-methyltetrahydrothiopyranium trifluoromethanesulfonate (3.35 g, 9.83 mmol) in deoxygenated water (32 mL) was added a solution of 1M NaOH (10.8 mL, 10.8 mmol) dropwise. After stirring for 1 hr at 0° C., the pH was adjusted to 7.5 with 1N HCl. The solution was lyophylized to give the desired thiol plus a mixture of salts. The product was used as such without further purification: 1Hmr (D2O) δ: 2.0-4.0 (m, 11H), 2.90 (s, 3H, SCH3) and 1.9 ppm (s, 3H, CH3CO-).

Sources & evidence

ORD record
ord-9ba91b80a9e545469a0990d75b679424
Source dataset
uspto-grants-1987_05
Patent number
US04665169

Reaction notes

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