1,1'-Thiocarbonyldiimidazole → 3-(Imidazol-1-yl)-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide imidazolium salt

HRID 1066142Notes

Reaction equation

HRID 1066142 reaction equation
NC1C=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].[C:15]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=S>O1CCOCC1>[NH+:17]1[CH:21]=[CH:20][NH:19][CH:18]=1.[N:22]1([C:15]2[NH:17][C:21]3[CH:20]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=3[S:11](=[O:13])(=[O:12])[N:14]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 153583862-Amino-5-nitrobenzenesulfonamide

Product 1

HCID 702374163-(Imidazol-1-yl)-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide imidazolium saltYield 68.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a hot solution of 2-amino-5-nitrobenzenesulfonamide (5 g) in dioxane (150 mL) was added thiocarbonyidiimidazole (14 g) and the reaction mixture was refluxed for 5 h. After cooling, the precipitate of the title compound was collected by filtration, washed with dioxane and dried to give the title compound (yield 5.7 g ); m.p. 246-248° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate of the title compound was collected by filtration
  4. washwashed with dioxane
  5. customdried

Sources & evidence

ORD record
ord-e6a5a0dd800e427aaa2c86bf38d319db
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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