Methanesulfonic Acid → HCID 20203369, compound

HRID 485227Notes

Reaction equation

HRID 485227 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.[CH3:8][S:9]([OH:12])(=[O:11])=[O:10].[CH2:13]1[S:15][CH2:14]1>O>[CH3:8][S:9]([O-:12])(=[O:11])=[O:10].[CH3:1][N+:2]1([CH2:13][CH2:14][SH:15])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 9865ThiiraneHCID 523249N-Methylthiomorpholine

Product 1

HCID 20203369HCID 20203369, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To precooled (ice bath) N-methylthiomorpholine* (500 g, 42.7 mmol) was added methanesulfonic acid (1.47 mL, 20.5 mmol) and ethylene sulfide (1.30 mL, 21.4 mmol). The mixture was heated at 65° C. for 24 h and diluted with water (25 mL). The aqueous solution was washed with diethyl ether (3×25 mL), pumped under vacuum and poured over a silica gel reverse phase column; the title compound being eluted with water. The appropriate fractions were combined and evaporated to afford the thiol as an oil (4.80 g, yield 86%); ir (film) νmax : 2550 cm-1 (w,SH); 1Hmr (DMSO d6)δ: 3.25-2.95 (6H, m, CH2N⊕), 3.32 (3H, s, CH3N⊕), 3.20-2.65 (7H, m, CH2S, SH) and 2.32 ppm (3H, s, CH3SO3).

Workup

  1. washThe aqueous solution was washed with diethyl ether (3×25 mL)
  2. additionpoured over a silica gel reverse phase column
  3. washthe title compound being eluted with water
  4. customevaporated

Sources & evidence

ORD record
ord-a827329d48224e748c7837888cb10ee4
Source dataset
uspto-grants-1985_08
Patent number
US04536335

Reaction notes

Loading…