Methyl iodide → 3-(methylthio)-6-nitro-1-phenyl-1H-indazole

HRID 68676Notes

Reaction equation

HRID 68676 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[S:19])[NH:9][N:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:20]([O-])([O-])=O.[Cs+].[Cs+].IC>CC#N>[CH3:20][S:19][C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 49839976HCID 49839976, compound

Product 1

HCID 674475223-(methylthio)-6-nitro-1-phenyl-1H-indazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
10 °C

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 6-nitro-1-phenyl-1,2-dihydroindazole-3-thione (3.1 g, 11.44 mmol, 1.00 equiv) in CH3CN (20 mL), Cs2CO3 (21 g, 64.42 mmol, 5.63 equiv). To the resulting mixture was then added a solution of iodomethane (11.3 g, 79.58 mmol, 6.96 equiv) in CH3CN (15 mL) dropwise with stirring at 10° C. in 30 min. The resulting solution was stirred for 30 min at 10° C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100) to yield 3-(methylthio)-6-nitro-1-phenyl-1H-indazole as a yellow solid. MS: 285 (MH+).

Workup

  1. customInto a 100-mL 3-necked round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 30 min at 10° C
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-720b6ffa7fa14f2f9182563083e02125
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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