Methyl iodide → 2-(4-chlorophenyl)-6-methoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

HRID 477879Notes

Reaction equation

HRID 477879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[NH:12][C:11]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:10]=3[S:9]2(=[O:22])=[O:21])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:25])[C:11]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:10]=3[S:9]2(=[O:21])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 198725922-(4-chlorophenyl)-6-methoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

Product 1

HCID 198725932-(4-chlorophenyl)-6-methoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-6-methoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (23.50 g) in dried N,N-dimethylformamide (150 ml) was added sodium hydride (60% oil dispersion) in one portion at 0° C. The suspension was stirred for one hour at ambient temperature and then methyl iodide (5.18 ml) was added therein at the same temperature. The reaction mixture was stirred for one and half hours a ambient temperature and then poured into ice water. The separated solid was filtered, dried and recrystrallized from ethanol to yield 2-(4-chlorophenyl)-6-methoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (21.07 g) as a white needle crystal.

Workup

  1. stirringThe reaction mixture was stirred for one and half hours a ambient temperature
  2. filtrationThe separated solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-12cb5d95901a440b98ba54b762c1dc4c
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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