Water → HCID 20266437, compound

HRID 1719712Notes

Reaction equation

HRID 1719712 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][S:18]2(=[O:23])=[O:22])=[CH:11][CH:10]=1.O.[BH4-].[Na+]>C(O)C>[CH2:1]([N:9]1[CH2:10][CH:11]=[C:12]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][S:18]2(=[O:23])=[O:22])[CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 202664342-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2-thiazolidine-1,1-dione

Product 1

HCID 20266437HCID 20266437, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl bromide (3.1 cm3) was added at room temperature to a stirred solution of 2-[2-(4-pyridyl)ethyl]isothiazolidine-1,1-dioxide (4.9 g) in ethanol (30 cm3) and the mixture was heated under reflux for 3 hours. After cooling to room temperature, water (30 cm3) was added followed by sodium borohydride (1.2 g) and the mixture was stirred for 1 hour. Volatile material was removed in vacuo and the residue was treated with 2M hydrochloric acid to pH1, followed by neutralisation with sodium carbonate solution and subsequent extraction with chloroform (3×100 cm3). The dried (MgSO4) chloroform extract was evaporated to give an oil which was chromatographed on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:49, to give 2-[2-(1-benzyl-1,2,3,6-tetrahydropyrid-4-yl)ethyl]isothiazolidine-1,1-dioxide as an oil (4.5 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customVolatile material was removed in vacuo
  4. additionthe residue was treated with 2M hydrochloric acid to pH1
  5. extractionfollowed by neutralisation with sodium carbonate solution and subsequent extraction with chloroform (3×100 cm3)
  6. dry with materialThe dried (MgSO4) chloroform
  7. extractionextract
  8. customwas evaporated
  9. customto give an oil which
  10. customwas chromatographed on silica ("Merck" 60.9385)
  11. washeluting with methanol

Sources & evidence

ORD record
ord-4152b37aecf44aac816bee5d5de1703a
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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