2-Amino-5-chlorobenzenesulphonamide → 4'-(2-Dimethylaminoethyl)-7-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-1,1-dioxide

HRID 903141Notes

Reaction equation

HRID 903141 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH3:13][N:14]([CH3:24])[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>Cl>[CH3:24][N:14]([CH3:13])[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][C:20]2([NH:1][C:2]3[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=3[S:9](=[O:11])(=[O:10])[NH:12]2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 122955502-Amino-5-chlorobenzenesulphonamideHCID 233377864-(2-Dimethylaminoethyl)cyclohexanone

Product 1

HCID 233377834'-(2-Dimethylaminoethyl)-7-chlorospiro[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-amino-5-chlorobenzenesulfonamide (8.0 g., 0.039 mole) and 4-(2-dimethylaminoethyl)cyclohexanone (13.5 g., 0.08 mole) in 0.6 N ethanolic HCl (110 ml.) is heated at reflux 18 hours. The solvent is evaporated at reduced pressure and the residue dissolved in water (100 ml.) and neutralized with sodium hydroxide to precipitate 4'-(2-dimethylaminoethyl)-7-chlorospiro-[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-1,1-dioxide hemisemihydrate which melts at 234°-5° C. after recrystallization from n-propanol.

Workup

  1. temperatureis heated
  2. temperatureat reflux 18 hours
  3. customThe solvent is evaporated at reduced pressure
  4. dissolutionthe residue dissolved in water (100 ml.)
  5. customto precipitate 4'-(2-dimethylaminoethyl)-7-chlorospiro-[2H-1,2,4-benzothiadiazine-3(4H),1'-cyclohexane]-1,1-dioxide hemisemihydrate which melts at 234°-5° C.
  6. customafter recrystallization from n-propanol

Sources & evidence

ORD record
ord-2d2a3a964fa44afc9bb5b120a155b634
Source dataset
uspto-grants-1980_10
Patent number
US04226867

Reaction notes

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