Sodium hydride → 2-(4-Chlorobutyl)-1lambda6-naphtho[1,8-CD]isothiazole-1,1(2H)-dione

HRID 1087490Notes

Reaction equation

HRID 1087490 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].[H-].[Na+].BrCCC[CH2:25][Cl:26].C1C=C2NS(C3=CC=CC(=C23)C=1)(=O)=O>CN(C)C=O>[Cl:26][CH2:25][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]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 690522H-Naphth(1,8-cd)isothiazole 1,1-dioxideHCID 813641-Bromo-4-chlorobutaneHCID 145800262(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 28004062-(4-Chlorobutyl)-1lambda6-naphtho[1,8-CD]isothiazole-1,1(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Chlorobutyl)naphtho[1,8-cd]isothiazole 1,1-dioxide may be obtained in the following manner: operating as in Example 1 for the preparation of 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide, starting with sodium hydride (4.8 g) in a 50% dispersion in vaseline oil, 1-bromo-4-chlorobutane (11.9 cc) and 1,8-naphthosultam (20.5 in dimethylformamide (250 cc). After purification by flash-chromatography on a silica under a current of argon at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and cyclohexanone (30-70 vol) as eluant, 2-(4-chlorobutyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (24.6 g) is obtained in the form of a yellow oil which is used in the crude state in the subsequent syntheses.

Workup

  1. customAfter purification by flash-chromatography on a silica under a current of argon at medium pressure (0.5-1.5 bar)
  2. additionwith a mixture of dichloromethane and cyclohexanone (30-70 vol) as eluant

Sources & evidence

ORD record
ord-d19669478c034d219fdeedc7208e4391
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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