Pseudosaccharin chloride → HCID 178422456, compound

HRID 1252538Notes

Reaction equation

HRID 1252538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.Cl[C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17](=[O:25])(=[O:24])[N:16]=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[S:17](=[O:24])(=[O:25])[N:16]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 64783Pseudosaccharin chlorideHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 178422456HCID 178422456, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a refluxing solution of 4-(5-bromo-3-methyl-2-pyridinyl)butylamine (1.87 g, 7.69 mmol) in chloroform (80 ml, freed of EtOH by passage through Woelm Grade I neutral alumina) was added over 50 minutes a solution of 3-chloro-1,2-benzisothiazole-1,1-dioxide (U.S. Pat. No. 4,490,527) (1.55 g, 7.69 mmol) in chloroform (50 ml, purified as above) while maintaining reflux. After the addition was complete, reflux was continued for another 15 minutes. Evaporation in vacuo gave a yellow orange foam. Crystallization from 2-propanol and recrystallization from methanol/methylene chloride/2-propanol (Norite) gave 2.07 g of the title compound as a tan solid hydrochloride: m.p. 232°-244° C., IR(KBr) 3070, 1610, 1578, 1508, 1280, 1140 cm-1. 1H NMR (Me2SO d6) 9.85 (1H, t), 8.70 (1H, s), 8.33 (1H, m), 8.27 (1H, s), 7.88 (3H, m) 3.40 (2H, m), 2.90 (2H, m), 2.37 (3H, s), 1.70 (4H, m).

Workup

  1. temperaturereflux
  2. additionAfter the addition
  3. temperaturereflux
  4. customEvaporation in vacuo
  5. customgave a yellow orange foam
  6. customCrystallization
  7. customfrom 2-propanol and recrystallization from methanol/methylene chloride/2-propanol (Norite)

Sources & evidence

ORD record
ord-e0014efcdf014145b3fc3970e5be6b77
Source dataset
uspto-grants-1988_05
Patent number
US04743692

Reaction notes

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