Sodium Iodide → 2-{3-[4-(4-Fluorophenyl)-1-piperazinyl]-2-methylpropyl}naptho[1,8-cd]isothiazole 1,1-dioxide

HRID 1087521Notes

Reaction equation

Cl[CH2:2][CH:3]([CH3:19])[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(CC)CC)C.[I-].[Na+].[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[F:29][C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:41][CH2:40][N:39]([CH2:2][CH:3]([CH3:19])[CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=45)[S:6]3(=[O:18])=[O:17])[CH2:38][CH2:37]2)=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The experiment is carried out as in Example 56, starting with 2-(3-chloro-2-methylpropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (10.4 g), triethylamine (5.1 cc), sodium iodide (5.4 g) and 4-(4-fluorophenyl)piperazine (6.5 g) in toluene (130 cc). The mixture is heated at boiling point for 16 hours, 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 dichloromethane and then ethyl acetate as eluants, and recrystallization from boiling acetonitrile (20 cc), 2-{3-[4-(4-fluorophenyl)-1-piperazinyl]-2-methylpropyl}naptho[1,8-cd]isothiazole 1,1-dioxide (3.1 g) is obtained m.p. 133° C.

Workup

temperatureThe mixture is heated
customfor 16 hours
customAfter purification by flash chromatography on a silica column
customunder a current of argon at medium pressure (0.5-1.5 bar) with dichloromethane and then ethyl acetate as eluants, and recrystallization

Sources & evidence

ORD record: ord-8c31dcc4316d4816ad910801c3a9664d
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036075

Reaction notes

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