2-Chloroethyl methyl sulfide → 1,3(2H,4H)-Isoquinolinedione, 4,4-dimethyl-2-(2-(methylthio)ethyl)-

HRID 1448037Notes

Reaction equation

HRID 1448037 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]1=[O:13].Cl[CH2:16][CH2:17][S:18][CH3:19].[Na]>C(O)(C)C>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:16][CH2:17][S:18][CH3:19])[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 109652-Chloroethyl methyl sulfideHCID 3380304,4-Dimethyl-1,3(2H,4H)-isoquinolinedioneHCID 5360545Sodium

Product 1

HCID 30534781,3(2H,4H)-Isoquinolinedione, 4,4-dimethyl-2-(2-(methylthio)ethyl)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.7 gm of 4,4-dimethyl-2H,4H-isoquinoline-1,3-dione and 3.3 gm of 1-chloro-2-methylmercapto-ethane were added to a solution of 0.7 gm of sodium in 200 ml of isopropanol. After refluxing the mixture for 3 hours the solvent was removed in vacuo, and the residue was taken up in water and chloroform. The separated organic phase was worked up as described in Example 1. Yield: 7 gm (88.6% of theory).

Workup

  1. temperatureAfter refluxing the mixture for 3 hours the solvent
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-abf42b0ca8c44f5d85f3451ac250f5de
Source dataset
uspto-grants-1979_12
Patent number
US04179508

Reaction notes

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