4-Amino-6-chloro-1,3-benzenedisulfonamide → 4'-dimethylamino-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide

HRID 903137Notes

Reaction equation

HRID 903137 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[S:13]([NH2:16])(=[O:15])=[O:14].[CH3:17][N:18]([CH3:26])[CH:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1>Cl>[CH3:17][N:18]([CH3:26])[CH:19]1[CH2:24][CH2:23][C:22]2([NH:1][C:2]3[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([NH2:12])(=[O:10])=[O:11])=[CH:4][C:3]=3[S:13](=[O:15])(=[O:14])[NH:16]2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 671364-Amino-6-chloro-1,3-benzenedisulfonamideHCID 103745454-(Dimethylamino)cyclohexan-1-one

Product 1

HCID 233377844'-dimethylamino-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-amino-6-chloro-1,3-benzenedisulfonamide (5.72 g., 0.02 mole) and 4-dimethylaminocyclohexanone (3.38 g., 0.022 mole) in 2 N ethanolic HCl (100 ml) is refluxed for one hour and cooled. 4'-Dimethylamino-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide hydrochloride is filtered, dissolved in warm water (200 ml.) and treated with aqueous ammonia (1.0 ml.) to give 4'-dimethylamino-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide which melts at 255° C. after recrystallization from dimethylsulfoxide--H2O.

Workup

  1. temperatureis refluxed for one hour
  2. temperaturecooled
  3. filtration4'-Dimethylamino-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide hydrochloride is filtered
  4. dissolutiondissolved in warm water (200 ml.)
  5. additiontreated with aqueous ammonia (1.0 ml.)

Sources & evidence

ORD record
ord-be844c9b34fc409186e621978b81fbf0
Source dataset
uspto-grants-1980_10
Patent number
US04226867

Reaction notes

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