Benzyltrimethylammonium hydroxide → 2-[2-(Pyridin-4-yl)propyl]-1lambda~6~,2-thiazolidine-1,1-dione

HRID 1154316

Reaction equation

HRID 1154316 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)([CH3:3])=[CH2:2].[S:10]1(=[O:16])(=[O:15])[CH2:14][CH2:13][CH2:12][NH:11]1.[OH-].C[N+](C)(C)CC1C=CC=CC=1>O.C(Cl)(Cl)Cl>[N:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH2:2][N:11]2[CH2:12][CH2:13][CH2:14][S:10]2(=[O:16])=[O:15])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 529351Pyridine, 4-(1-methylethenyl)HCID 6421571,3-Propanesultam

Product 1

HCID 204349382-[2-(Pyridin-4-yl)propyl]-1lambda~6~,2-thiazolidine-1,1-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A mixture of 4-isopropenyl pyridine (1.79 g) and isothiazolidine-1,1-dioxide (1.81 g) was heated at 130° C. during the addition of "Triton B" (Trade Mark, trimethylbenzylammonium hydroxide) (0.25 g added every hour for four hours; 40% solution in water). After stirring for 16 hours at 130° the mixture was cooled and taken in chloroform (50 cm3) and water (50 cm3). The aqueous phase was extracted with chloroform (3×20 cm3) and the dried (MgSO4) extracts were evaporated to given an oil. Chromatography on silica ("Merck 60. 9385") eluting with ethyl acetate gave 2-[2-(4-pyridyl)prop-1-yl]isothiazolidine-1,1-dioxide which crystallised from ethyl acetate-hexane as needles, m.p. 90°-92° (1.01 g).

Workup

  1. additionadded every hour for four hours
  2. temperaturewas cooled
  3. extractionThe aqueous phase was extracted with chloroform (3×20 cm3)
  4. dry with materialthe dried (MgSO4) extracts
  5. customwere evaporated
  6. washChromatography on silica ("Merck 60. 9385") eluting with ethyl acetate

Sources & evidence

ORD record
ord-7058774eda464732bce4cd4405a853c3
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Linked notes

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