Sodium Bicarbonate → HCID 19817091, compound

HRID 1493277Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=23)[S:5]1(=[O:17])=[O:16].Br.Br.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[OH:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][N:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[C:12]5[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=45)[S:5]3(=[O:17])=[O:16])[CH2:29][CH2:28]2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(2-chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 g), 4-(4-hydroxyphenyl)piperazine dihydrobromide (3.4 g) and sodium bicarbonate (1.3 g) in dimethylformamide (30 cc). The mixture is heated for 4 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 (90 cc), 2-(2-[4-(4-hydroxyphenyl)-1-piperazin-Yl]ethyl}naphtho[1-,8-cd]isothiazole 1,1-dioxide (1.6 g) is obtained, m.p. 235° C.

Workup

temperatureThe mixture is heated for 4 hours
customAfter purification by flash-chromatography on a silica column
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-0428fe6942c14de4887dc1abfe1fc2bc
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021420

Reaction notes

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