Water → HCID 70873236, compound

HRID 2280113Notes

Reaction equation

HRID 2280113 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[C:5]([SH:8])=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:17]1[C:18](=[O:25])[N:19]([CH3:24])[C:20](=[O:23])[C:21]=1Cl.O>CN(C=O)C>[CH3:24][N:19]1[C:20](=[O:23])[C:21]2[S:9][C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=3[S:8][C:17]=2[C:18]1=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 103343,4-ToluenedithiolHCID 11430Potassium CarbonateHCID 142932,3-Dichloro-N-methylmaleimide

Product 1

HCID 70873236HCID 70873236, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of 4-methylbenzene-1,2-dithiol (0.5 g) in anhydrous DMF (50 ml) was treated with K2CO3 and 3,4-dichloro-1-methyl-pyrrole-2,5-dione (0.73 g) and stirred for about 7 hours at 80° C. The reaction mixture was poured into water and extracted with MTBE. The combined organic phases were washed once with water and after removal of the solvent under reduced pressure the crude product (0.85 g) was purified by flash column chromatography on silica gel (cyclohexane/ethyl acetate 9:1) to yield the compound ex. I-2 (0.25 g); m.p.: 171-176° C.

Workup

  1. extractionextracted with MTBE
  2. washThe combined organic phases were washed once with water
  3. customafter removal of the solvent under reduced pressure the crude product (0.85 g)
  4. customwas purified by flash column chromatography on silica gel (cyclohexane/ethyl acetate 9:1)
  5. customto yield the compound ex

Sources & evidence

ORD record
ord-19ccc163bd0e4738b90e6f2ce9679cbf
Source dataset
uspto-grants-2015_09
Patent number
US09137997B2

Reaction notes

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