Succinimide → 4-Chloro-2-(1,1,3,3-tetramethylbutyl)-3(2H)-isothiazolone

HRID 2231606Notes

Reaction equation

HRID 2231606 reaction equation
[C:1]([N:9]1[C:13](=[O:14])[CH:12]=[CH:11][S:10]1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Cl:15]N1C(=O)CCC1=O.C1(=O)NC(=O)CC1>C(Cl)(Cl)Cl>[Cl:15][C:12]1[C:13](=[O:14])[N:9]([C:1]([CH2:4][C:5]([CH3:7])([CH3:8])[CH3:6])([CH3:2])[CH3:3])[S:10][CH:11]=1

Participants

5

Reactant 3

HCID 11439SuccinimideHCID 31398ChlorosuccinimideHCID 21822474HCID 21822474, compound

Product 1

HCID 198844224-Chloro-2-(1,1,3,3-tetramethylbutyl)-3(2H)-isothiazolone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 10.7 g. (0.05 mole) of 2-t-octyl-3-isothiazolone in 100 ml. of chloroform is added in a single portion 13.3 g. (0.1 mole) of N-chlorosuccinimide. The mixture warms somewhat but does not require cooling. After stirring for 2.5 hours, the mixture is filtered giving 7.5 g. of crude succinimide. The filtrate is evaporated under reduced pressure and the residue dissolved in ether. The ether solution is extracted with water, dried over anhydrous magnesium sulfate, and evaporated to a mixture of solid and oil. The oil is washed from the solid with hexane leaving 1.7 g. (14%) of white 4-chloro-2-t-octyl-3-isothiazolone, m.p. 137°-140°.

Workup

  1. temperaturedoes not require cooling
  2. filtrationthe mixture is filtered
  3. customgiving 7.5 g
  4. customThe filtrate is evaporated under reduced pressure
  5. dissolutionthe residue dissolved in ether
  6. extractionThe ether solution is extracted with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated to a mixture of solid and oil
  9. washThe oil is washed from the solid with hexane leaving 1.7 g

Sources & evidence

ORD record
ord-42edde3544c8469195dfe9ec4c4b650d
Source dataset
uspto-grants-1988_11
Patent number
US04783221

Reaction notes

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