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

HRID 903140Notes

Reaction equation

HRID 903140 reaction equation
[CH3:1][NH:2][CH:3]([CH3:12])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1.[NH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:16][C:15]=1[S:25]([NH2:28])(=[O:27])=[O:26]>Cl>[ClH:20].[CH3:1][NH:2][CH:3]([CH3:12])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8]2([NH:13][C:14]3[CH:19]=[C:18]([Cl:20])[C:17]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:16][C:15]=3[S:25](=[O:27])(=[O:26])[NH:28]2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 671364-Amino-6-chloro-1,3-benzenedisulfonamideHCID 537818444-(2-Methylaminopropyl) cyclohexanone

Product 1

HCID 233377984'-(2-Methylaminopropyl)-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-(2-methylaminopropyl) cyclohexanone (4.0 g., 0.024 mole) and 4-amino-6-chloro-1,3-benzenedisulfonamide (4.4 g., 0.0154 mole) in 2 N ethanolic HCl (75 ml.) is refluxed for one hour and cooled to give 7.0 g. of 4'-(2-methylaminopropyl)-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H)-1'-cyclohexane]-7-sulfonamide-1,1-dioxide hydrochloride which melts at 296° C.

Workup

  1. temperatureis refluxed for one hour
  2. temperaturecooled
  3. customto give 7.0 g

Sources & evidence

ORD record
ord-6c3fd071d4714af1be49aa23e12dfad8
Source dataset
uspto-grants-1980_10
Patent number
US04226867

Reaction notes

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