Triethylamine → 2-([2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]piperid-4-yl)-1,2-benzoisothiazolin-3-one-1,1-dioxide

HRID 66558Notes

Reaction equation

HRID 66558 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:14])[CH2:12]Br.Cl.[NH:16]1[CH2:21][CH2:20][CH:19]([N:22]2[C:26](=[O:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[S:23]2(=[O:33])=[O:32])[CH2:18][CH2:17]1.C(N(CC)CC)C>C(O)C.C(O)(C)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:14])[CH2:12][N:16]1[CH2:17][CH2:18][CH:19]([N:22]2[C:26](=[O:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[S:23]2(=[O:32])=[O:33])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 126085902-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-olHCID 705454252-(Piperid-4-yl)-1,2-benzisothiazolin-3-one-1,1-dioxide hydrochloride

Product 1

HCID 130189812-([2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]piperid-4-yl)-1,2-benzoisothiazolin-3-one-1,1-dioxide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

Erythro 1-(1,4-Benzodioxan-2-yl)-2-bromoethanol (1.29 g, 0.005 m), 2-(piperid-4-yl)-1,2-benzisothiazolin-3-one-1,1-dioxide hydrochloride (1.44 g, 0.005 m) and triethylamine (4 cm3) were refluxed for 24 hours in ethanol (50 cm3). The solution was cooled, the solvent evaporated and the residue treated with water. The product was extracted with chloroform, washed with water and dried (MgSO4). Evaporation gave a gum which was dissolved in isopropyl alcohol. The crystallised solid was collected by filtration, dissolved in ethanol and treated with ethanolic HCl. Ether was added and the resulting precipitate filtered off and recrystallised from isopropyl alcohol to give the title compound as the hydrochloride salt, m.p. 216°-218° C.

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent evaporated
  3. additionthe residue treated with water
  4. extractionThe product was extracted with chloroform
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation
  8. customgave a gum which
  9. filtrationThe crystallised solid was collected by filtration
  10. dissolutiondissolved in ethanol
  11. additiontreated with ethanolic HCl
  12. additionEther was added
  13. filtrationthe resulting precipitate filtered off
  14. customrecrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-f0620e0b83b64ccfbcc7d52bfc7bde39
Source dataset
uspto-grants-1982_08
Patent number
US04342761

Reaction notes

Loading…