Potassium Carbonate → 7-(1,1-Dioxo-2h-naphtho[1,8-cd]isothiazol-2-yl)-heptanoic acid benzyloxyamide

HRID 9084Notes

Reaction equation

HRID 9084 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[CH:24]=[C:23]2[NH:25][S:26]([C:29]3=[CH:30][CH:31]=[CH:32][C:21](=[C:22]23)[CH:20]=1)(=[O:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:25]1[C:23]2[CH:24]=[CH:19][CH:20]=[C:21]3[CH:32]=[CH:31][CH:30]=[C:29]([C:22]=23)[S:26]1(=[O:27])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 690522H-Naphth(1,8-cd)isothiazole 1,1-dioxideHCID 865865457-Bromo-heptanoic acid benzyloxyamide

Product 1

HCID 879016657-(1,1-Dioxo-2h-naphtho[1,8-cd]isothiazol-2-yl)-heptanoic acid benzyloxyamide

Procedure

In a manner analogous to that of example 1(b), 7-bromo-heptanoic acid benzyloxyamide 0.46 g, 1.5 mmol) was reacted with 1,8-naphthalenesultam (0.3 g, 1.5 mmol) in the presence of potassium carbonate (0.2 g, 1.4 mmol) to give 7-(1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-heptanoic acid benzyloxyamide as an amorphous solid (yield 0.4 g, 62%; purified by column chromatography using silica gel and ethyl acetate:heptane=1:1 as an eluent). MS (M+H+)=439.

Sources & evidence

ORD record
ord-190bbd673a414296bb77ded29b4d23dd
Source dataset
uspto-grants-2006_08
Patent number
US07091229B2

Reaction notes

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