1,1'-Carbonyldiimidazole → 2-(4-chlorophenyl)-6-methoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

HRID 477878Notes

Reaction equation

HRID 477878 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)(=[O:12])=[O:11].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>O1CCOCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:21](=[O:22])[NH:1][C:2]3[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=3[S:10]2(=[O:12])=[O:11])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 198725182-amino-4-methoxy-N-(4-chlorophenyl)-benzenesulfonamide

Product 1

HCID 198725922-(4-chlorophenyl)-6-methoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxideYield 90.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-4-methoxy-N-(4-chlorophenyl)-benzenesulfonamide (24.37 g) and 1,1'-carbonyldiimidazole (18.93 g) in dried dioxane (500 ml) was refluxed overnight and then concentrated to dryness. The residue was washed with methanol and collected by filtration to yield 2-(4-chlorophenyl)-6-methoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (23.9 g).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated to dryness
  3. washThe residue was washed with methanol
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-34ff190ad66440e08a6c197441587f9e
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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