Acetonitrile → HCID 178422457, compound

HRID 1252539Notes

Reaction equation

HRID 1252539 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]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=2[S:17](=[O:26])(=[O:25])[N:16]=1.C(#N)C>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]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[S:17](=[O:25])(=[O:26])[N:16]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineHCID 13390869HCID 13390869, compound

Product 1

HCID 178422457HCID 178422457, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a refluxing solution of 4-(5-bromo-3-methyl-2-pyridinyl)butylamine (300 mg, 1.23 mmol) in chloroform (20 ml, purified as in previous example) was added over 10 minutes a solution of 3,5-dichloro-1,2-benzisothiazole 1,1-dioxide (U.S. Pat. No. 4,490,527) (400 mg, 1.69 mmol) in chloroform (20 ml)/acetonitrile (10 ml). Since a precipitate formed during the addition, another 10 ml of acetonitrile was added to give almost complete solution. Heating at 65°-70° C. was continued for 60 minutes giving a slightly cloudy mixture. Cooling to room temperature, filtration and evaporation of the filtrate in vacuo gave a solid residue. Recrystallization from methanol/methylene chloride/2-propanol gave 0.410 g of the title compound as an off-white solid hydrochloride: m.p. 231°-235° C., IR(KBr) 3005, 2500 (broad), 1620, 1278, 1160 cm-1. 1H NMR (Me2SO-d6) 9.87 (1H, t), 8.68 (1H, s), 8.60 (1H, s), 8.25 (1H, s), 7.90 (2H, m), 3.42 (2H, m), 2.83 (2H, m), 2.37 (3H, s), 1.68 (4H, m).

Workup

  1. customwas added over 10 minutes
  2. customSince a precipitate formed during the addition
  3. customto give almost complete solution
  4. temperatureHeating at 65°-70° C.
  5. customgiving a slightly cloudy mixture
  6. filtrationfiltration and evaporation of the filtrate in vacuo
  7. customgave a solid residue
  8. customRecrystallization from methanol/methylene chloride/2-propanol

Sources & evidence

ORD record
ord-e6036933cb3a4f409098d103793294b6
Source dataset
uspto-grants-1988_05
Patent number
US04743692

Reaction notes

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