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

HRID 903139Notes

Reaction equation

HRID 903139 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]([CH3:28])[CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>Cl>[ClH:8].[CH3:28][N:18]([CH3:17])[CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][C:24]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)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 671364-Amino-6-chloro-1,3-benzenedisulfonamideHCID 233377864-(2-Dimethylaminoethyl)cyclohexanone

Product 1

HCID 233377974'-(2-dimethylaminoethyl)-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-amino-6-chloro-1,3-benzenedisulfonamide (4.3 g., 0.015 mole) and 4-(2-dimethylaminoethyl) cyclohexanone (3.0 g., 0.018 mole) in 3 N ethanolic HCl (50 ml.) is refluxed for one and one half hours and cooled to give 4'-(2-dimethylaminoethyl)-6-chlorospiro-[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide hydrochloride (m.p. 279°-81° C.) which is dissolved in warm water (300 ml.) and treated with aqueous ammonia (1 ml.) to give 4'-(2-dimethylaminoethyl)-6-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-7-sulfonamide-1,1-dioxide which melts at 238°-9° C. after recrystallization from dimethylformamide-water.

Workup

  1. temperatureis refluxed for one and one half hours
  2. temperaturecooled

Sources & evidence

ORD record
ord-27d1bc67138740288cc6e679b4b273a8
Source dataset
uspto-grants-1980_10
Patent number
US04226867

Reaction notes

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