Methanesulfonic Acid → HCID 20159242, compound

HRID 1583517Notes

Reaction equation

HRID 1583517 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:9][S:10]([OH:13])(=[O:12])=[O:11].[CH2:14]1[S:16][CH2:15]1>O>[CH3:9][S:10]([O-:13])(=[O:12])=[O:11].[SH:16][CH2:15][CH2:14][N+:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 9865ThiiraneHCID 237193-Methoxypyridine

Product 1

HCID 20159242HCID 20159242, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To precooled (5° C.) 3-methoxypyridine (698 mg, 6.4 mmol) was added dropwise methanesulfonic acid (0.216 mL, 3.05 mmol) and ethylene sulfide (0.19 mL, 3.2 mmol). The mixture was then heated at 60° C. for 18 h, cooled to 20° C., diluted with water (10 mL) and washed with ether (3×10 mL). The aqueous phase was pumped under high vacuum for 15 min and poured on a C18 reverse phase column. The title compound was eluted with water. The appropriate fractions were combined and evaporated under high vacuum to give the desired thiol (61.6 mg, yield 76.3%); ir (CH2Cl2) νmax :2550 (w, SH) and 1620, 1600, 1585 cm-1 (m, aromatic); 1Hmr (DMSO d6) δ: 8.90-7.90 (4H, m, aromatic C-H), 4.72 (2H, t, J=6.6 Hz, CH2N+), 4.01 (3H, s, OCH3), 3.5-3.0 (m, hidden CH2S), 2.66 (1H, dd, J=9.6 Hz, J=7.5 Hz, SH) and 2.31 ppm (3H, s, CH3SO3).

Workup

  1. temperaturecooled to 20° C.
  2. washwashed with ether (3×10 mL)
  3. additionpoured on a C18 reverse phase column
  4. washThe title compound was eluted with water
  5. customevaporated under high vacuum

Sources & evidence

ORD record
ord-98704978a71d4022a09270cf83b83a63
Source dataset
uspto-grants-1985_11
Patent number
US04552696

Reaction notes

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