Triethylamine → 3-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl-oxysulfonyl)-1,2,4-triazole

HRID 260347Notes

Reaction equation

HRID 260347 reaction equation
[CH3:1][C:2]1([CH3:12])[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.C(N(CC)CC)C.Cl[S:21]([C:24]1[N:28]=[CH:27][NH:26][N:25]=1)(=[O:23])=[O:22]>O1CCCC1>[CH3:1][C:2]1([CH3:12])[C:6]2[CH:7]=[C:8]([O:11][S:21]([C:24]3[N:28]=[CH:27][NH:26][N:25]=3)(=[O:23])=[O:22])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 224014503,3-Dimethyl-2,3-dihydro-1-benzofuran-5-olHCID 178527437HCID 178527437, compound

Product 1

HCID 1784288433-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl-oxysulfonyl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.4 g of 3,3-dimethyl-5-hydroxy-2,3-dihydrobenzofuran was dissolved in 30 ml of tetrahydrofuran, and then 4.6 ml of triethylamine was added while stirring the solution. Then, 5.0 g of 3-chlorosulfonyl-1,2,4-triazole was gradually added while cooling with ice and stirring the solution. Then, this was stirred for 14 hours. Tetrahydrofuran was evaporated, and 2N hydrochloric acid was added and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate, and the solvent was removed, so that coarse crystals were obtained. This was then recrystallized from n-hexane/ethyl acetate, so that 2.7 g of the titled compound was obtained.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirring the solution
  3. stirringThen, this was stirred for 14 hours
  4. customTetrahydrofuran was evaporated
  5. addition2N hydrochloric acid was added
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried with magnesium sulfate
  9. customthe solvent was removed
  10. customso that coarse crystals were obtained
  11. customThis was then recrystallized from n-hexane/ethyl acetate, so that 2.7 g of the titled compound
  12. customwas obtained

Sources & evidence

ORD record
ord-b48b170192124475be4619b0ef856e34
Source dataset
uspto-grants-1996_06
Patent number
US05527818

Reaction notes

Loading…