Sodium Hydroxide → 2-[(Pyridin-4-yl)methyl]-1lambda~6~,2-thiazolidine-1,1-dione

HRID 1154318Notes

Reaction equation

HRID 1154318 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.[OH-].[Na+].[S:12]1(=[O:18])(=[O:17])[CH2:16][CH2:15][CH2:14][NH:13]1>O>[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:13]2[CH2:14][CH2:15][CH2:16][S:12]2(=[O:18])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 6421571,3-Propanesultam

Product 1

HCID 204349122-[(Pyridin-4-yl)methyl]-1lambda~6~,2-thiazolidine-1,1-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-picolylchloride hydrochloride (2.7 g) was stirred in water (10 cm3) with sodium hydroxide (1.3 g) during the addition of isothiazolidine-1,1-dioxide (2.0 g) in water (5 cm3). After stirring for 2 hours the mixture was extracted with chloroform (3×15 cm3) and the dried (MgSO4) extracts were evaporated in vacuo to give an oil which was chromatographed on silica (MK 60. 9385) eluting with ethyl acetate to give an oil which crystallised from ethyl acetate affording 2-(4-pyridylmethyl)isothiazolidine-1,1-dioxide as white crystals, m.p. 82° (3.5 g).

Workup

  1. extractionwas extracted with chloroform (3×15 cm3)
  2. dry with materialthe dried (MgSO4) extracts
  3. customwere evaporated in vacuo
  4. customto give an oil which
  5. customwas chromatographed on silica (MK 60. 9385)
  6. washeluting with ethyl acetate
  7. customto give an oil which
  8. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-a1f4a2c0eb33427baa78347cd0fa15a1
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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