Water → HCID 19872474, compound

HRID 477892Notes

Reaction equation

HRID 477892 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11]3[CH:16]=[C:17]([NH:20][CH3:21])[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:23])=[O:22])=[CH:4][CH:3]=1.[CH2:24]([Li])CCC.CI.O>C1COCC1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11]3[CH:16]=[C:17]([N:20]([CH3:24])[CH3:21])[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:22])=[O:23])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 19872550HCID 19872550, compoundHCID 178418339Butyllithium

Product 1

HCID 19872474HCID 19872474, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-chlorophenyl)-4-methyl-6-(N-methylamino)-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (55 mg) in dry THF (2 ml) was added a 1.5M solution of n-butyl lithium in n-Hexane (0.16 ml) at -78° C. The mixture was stirred at 0° C. for 30 minutes and added methyl iodide (0.05 ml) at the same temperature. After the mixture was stirred at 0° C. for 30 minutes, water was added. The mixture was extracted two times with ethyl acetate and the combined organic layers were washed with water and brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was purified by preparative thin layer chromatography (eluted with a mixture of benzene and acetone (9:1) to give 2-(4-chlorophenyl)-6-(N,N-dimethylamino)-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (8 mg) as colorless powder.

Workup

  1. stirringAfter the mixture was stirred at 0° C. for 30 minutes
  2. extractionThe mixture was extracted two times with ethyl acetate
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative thin layer chromatography (
  7. washeluted with a mixture of benzene and acetone (9:1)

Sources & evidence

ORD record
ord-0a0f250b1bf54951b45f8ad007caee52
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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