Sodium hydride → HCID 19817098, compound

HRID 1493265Notes

Reaction equation

HRID 1493265 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][S:7](=[O:15])(=[O:14])[C:8]3[C:9]=2[C:10]=1[CH:11]=[CH:12][CH:13]=3.[H-].[Na+].Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH:26]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH:24]=[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:26][CH2:27]3)[S:7](=[O:15])(=[O:14])[C:8]3[C:9]=2[C:10]=1[CH:11]=[CH:12][CH:13]=3

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98375831-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridineHCID 13278178HCID 13278178, compound

Product 1

HCID 19817098HCID 19817098, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The experiment is carried out as in Example 18, starting with 5-chloronaphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 g), sodium hydride (0.15 g) in an 80% dispersion in vaseline oil, 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (1.4 g), obtained as in Example 18, and dimethylformamide (30 cc). The reaction mixture is heated for one hour at 70° C., cooled to a temperature of about 20° C. then concentrated to dryness at 20° C. under reduced pressure (0.5 mm Hg; 0.07 kPa). The residue is redissolved in dichloromethane (100 cc) and the solution is washed with distilled water (50 cc), dried over magnesium sulphate and concentrated to dryness at 20° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is purified by chromatography on a silica column with a mixture of dichloromethane and ethyl acetate (90-10 vol) as eluant, and recrystallized from boiling acetonitrile (30 cc). 5-Chloro-2-[3-(4-phenyl-1,2,3,6tetrahydro-1-pyridyl)propyl]naphtho[1,8 -cd]isothiazole 1,1-dioxide (1 g) is obtained, m.p. 135° C.

Workup

  1. temperaturecooled to a temperature of about 20° C.
  2. concentrationthen concentrated to dryness at 20° C. under reduced pressure (0.5 mm Hg; 0.07 kPa)
  3. dissolutionThe residue is redissolved in dichloromethane (100 cc)
  4. washthe solution is washed with distilled water (50 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness at 20° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  7. customThe residue is purified by chromatography on a silica column with a mixture of dichloromethane and ethyl acetate (90-10 vol) as eluant
  8. customrecrystallized

Sources & evidence

ORD record
ord-ffa1d52b6cc84cfcaaf189cfee130240
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

Loading…