Methyl iodide → 5-(Methylthio)-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one

HRID 2050516Notes

Reaction equation

[S:1]=[C:2]1[N:12]2[C:13]3[N:8]([C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=4)=[CH:10][CH2:11]2)[N:7]=[CH:6][C:5]=3[C:4](=[O:24])[NH:3]1.[H-].[Na+].[CH3:27]I>O1CCCC1>[CH3:27][S:1][C:2]1[N:12]2[C:13]3[N:8]([C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=4)=[CH:10][CH2:11]2)[N:7]=[CH:6][C:5]=3[C:4](=[O:24])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 100 mg of 4,5-dihydro-5-thioxo-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one (Example 24) in 10 ml of dry tetrahydrofuran, cooled at 0° C., is added 13 mg of sodium hydride (60 percent dispersion in mineral oil). The reaction mixture is stirred at 0° C. for 15 minutes, then an excess of methyl iodide is added and the mixture is allowed to warm to room temperature and then is stirred for 3 hours. The mixture is quenched with water and extracted with chloroform and evaporation of the extract in vacuo gives 47 mg of the desired product mp 234-237° C. (with decomposition).

Workup

temperatureto warm to room temperature
stirringis stirred for 3 hours
customThe mixture is quenched with water
extractionextracted with chloroform and evaporation of the
extractionextract in vacuo

Sources & evidence

ORD record: ord-9a138ee8f25b47c28648167cdfa4eea8
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013737

Reaction notes

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