Toluene → HCID 14580031, compound

HRID 1493256Notes

Reaction equation

HRID 1493256 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=23)[S:6]1(=[O:18])=[O:17].C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[C:32]1(C)C=CC=CC=1>>[N:21]1[CH:22]=[CH:23][CH:32]=[CH:25][C:24]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=34)[S:6]2(=[O:18])=[O:17])[CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 4837PiperazineHCID 8471TriethylamineHCID 145800262(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 14580031HCID 14580031, compound

Conditions

Temperature
20 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (8.5 g), triethylamine (4.2 cc) and 1-2-pyridyl)piperazine (4.7 cc) in toluene (80 cc). The mixture is heated for 2 hours at boiling point, then cooled to a temperature of about 20° C. After purification by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as eluant, and recrystallization from boiling acetonitrile (30 cc), 2-{3-[4-(2-pyridyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (4.2 g) is obtained, m.p. 101° C.

Workup

  1. temperatureThe mixture is heated for 2 hours
  2. customAfter purification by flash-chromatography on a silica column
  3. customunder a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as eluant, and recrystallization

Sources & evidence

ORD record
ord-a3d753f4899b4d9ba8753b4f0b5c0e39
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

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