2,3-Dimethyl-1,3-butadiene → HCID 12477039, compound

HRID 2050034Notes

Reaction equation

HRID 2050034 reaction equation
[CH2:1]([N:9]1[C:13](=[O:14])[CH:12]=[CH:11][S:10]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:16][C:17]([C:19]([CH3:21])=[CH2:20])=[CH2:18]>C(Cl)CCl>[CH3:16][C:17]1[CH2:18][CH:12]2[C:13](=[O:14])[N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[S:10](=[O:15])[CH:11]2[CH2:20][C:19]=1[CH3:21]

Participants

4

Reactant 2

HCID 105662,3-Dimethyl-1,3-butadieneHCID 159604752-Octyl-1H-1lambda~4~,2-thiazole-1,3(2H)-dione

Product 1

HCID 12477039HCID 12477039, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2.2 g (0.01 mole) of 2-n-octyl-4-isothiazolin-3-one 1-oxide in 15 ml of ethylene dichloride is added 1.1 g (0.012 mole) of 2,3-dimethyl-1,3-butadiene. The solution is stirred and maintained at 60° C. overnight. The mixture is concentrated to give a dark, thick oil. The oil is further purified by column chromatography (90% benzene, 10% acetone, silica) to yield 1.58 g (51%) of product as a yellow oil.

Workup

  1. concentrationThe mixture is concentrated
  2. customto give a dark, thick oil
  3. customThe oil is further purified by column chromatography (90% benzene, 10% acetone, silica)

Sources & evidence

ORD record
ord-28404ea3b1684924a9bdac79e32e8ccb
Source dataset
uspto-grants-1980_04
Patent number
US04199591

Reaction notes

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