Tris(methylthio)methyl methyl sulfate → 3-[bis(methylthio)methylene]-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)quinoline-2,4(1H,3H)-dione

HRID 601329Notes

Reaction equation

HRID 601329 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[C:4](=[O:23])[CH:3]=1.S(OC)(O[C:28](SC)([S:31][CH3:32])[S:29][CH3:30])(=O)=O>C(O)(=O)C.N1C=CC=CC=1>[CH3:30][S:29][C:28]([S:31][CH3:32])=[C:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([N:12]2[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]2=[O:21])[C:4]1=[O:23]

Participants

4

Reactant 2

HCID 24976308Tris(methylthio)methyl methyl sulfateHCID 670638572-(4-hydroxy-2-oxoquinolin-1(2H)-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 103415063-[bis(methylthio)methylene]-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)quinoline-2,4(1H,3H)-dioneYield 66%

Reagents, catalysts & solvents 1

HCID 165292Pyridinium acetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the product of Example 350B (0.6 g, 1.96 mmol) in acetic acid:pyridine (5:1, 15 mL) was treated with tris(methylthio)methyl methyl sulfate (prepared using the procedures in Synthesis, 22-25, 1988; M. Barbero, S. Cadamuro, I. Degani, R. Fochi, A. Gatti, V. Regondi)(1.6 g, 3 eq.) and heated at 100° C. for 2 hours. The reaction mixture was treated with ice, and the precipitated solids were filtered and dried in vacuum to give 0.53 g (66%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.63 (s, 6H), 7.34 (m, 1H), 7.55 (d, 1H), 7.61 (m, 1H), 8.08 (m, 5H). MS (DCI+) m/z 411 (M+H)+.

Workup

  1. customprepared
  2. customin Synthesis, 22-25, 1988
  3. additionThe reaction mixture was treated with ice
  4. filtrationthe precipitated solids were filtered
  5. customdried in vacuum

Sources & evidence

ORD record
ord-46af057dd1564689a724ac4c6f729b08
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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