1,2-Oxathiolane, 3-methyl-, 2,2-dioxide → 2-Butanesulfonic acid, 4-(1H-benzimidazol-2-ylthio)-

HRID 239807Notes

Reaction equation

HRID 239807 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][CH:12]1[S:16](=[O:18])(=[O:17])[O:15][CH2:14][CH2:13]1>O1CCOCC1.O>[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:14][CH2:13][CH:12]([S:16]([OH:18])(=[O:17])=[O:15])[CH3:11]

Participants

5

Reactant 2

HCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxideHCID 178527775HCID 178527775, compound

Product 1

HCID 119765762-Butanesulfonic acid, 4-(1H-benzimidazol-2-ylthio)-Yield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a hot solution of 2-mercaptobenzimidazole (2.0 g, 13.3 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was added via syringe pump (1 hour addition) a solution of 2,4-butane sultone (1.80 g, 12.7 mmol in 1,4-dioxane (total of 3 mL)). The solution was stirred at reflux for an additional 3 hours. The solid was collected by filtration. It was washed with acetone (2×20 mL) and dried in vacuo. Yield: 86%. 1H NMR (DMSO, 500 MHz) δ ppm 7.64(m, 2H), 7.44 (m, 2H), 3.63 (t, 2H, J=7.3 Hz), 2.68 (m, 1H), 2.10 (m, 1H), 1.90 (m, 1H), 1.15 (d, 3H, J=6.8 Hz). 13C (DMSO, 125 MHz) δ ppm 152.64, 133.32, 125.66, 113.67, 53, 10, 39.72, 33.48, 30.14, 16.85. ES-MS 287 (M+1).

Workup

  1. temperatureat reflux for an additional 3 hours
  2. filtrationThe solid was collected by filtration
  3. washIt was washed with acetone (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-24a94286250e42faae6547c26383bdbd
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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