1,2-Dichloroethane → 3a,4,7,7a-tetrahydro-5,6-dimethyl-1,2-benzisothiazol-3-(2H)-one 1,1-dioxide

HRID 2050035Notes

Reaction equation

HRID 2050035 reaction equation
C(Cl)CCl.[S:5]1(=[O:12])(=[O:11])[CH:9]=[CH:8][C:7](=[O:10])[NH:6]1.[CH3:13][C:14]([C:16]([CH3:18])=[CH2:17])=[CH2:15]>CCOCC>[CH3:13][C:14]1[CH2:15][CH:8]2[C:7](=[O:10])[NH:6][S:5](=[O:12])(=[O:11])[CH:9]2[CH2:17][C:16]=1[CH3:18]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 105662,3-Dimethyl-1,3-butadieneHCID 124770343-Hydroxy-1lambda6,2-thiazole-1,1-dione

Product 1

HCID 124770383a,4,7,7a-tetrahydro-5,6-dimethyl-1,2-benzisothiazol-3-(2H)-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 40 ml solution of ethylene dichloride containing 5.3 g (0.04 mole) of 4-isothiazolin-3-one 1,1-dioxide and 3.3 g (0.04 mole) of 2,3-dimethyl-1,3-butadiene is heated at 45°-50° C. overnight. The golden solution is cooled and concentrated to give an oil. Trituration of the oil with ether gives a white solid, 7.7 g (80%), m.p. 110°-112° C., which can be recrystallized from ethyl acetate.

Workup

  1. temperatureThe golden solution is cooled
  2. concentrationconcentrated
  3. customto give an oil
  4. customcan be recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ee33686d00724b9c8b6290520687bc6f
Source dataset
uspto-grants-1980_04
Patent number
US04199591

Reaction notes

Loading…