Sodium hydride → HCID 14726791, compound

HRID 1087522Notes

Reaction equation

HRID 1087522 reaction equation
S1(=O)(=O)C=CC=N1.BrCC(O)CN1C2C=CC=C3C=CC=C(C=23)S1(=O)=O.[S:27]1(=[O:40])(=[O:39])[C:31]2=[CH:32][CH:33]=[CH:34][C:35]3=[CH:36][CH:37]=[CH:38][C:29](=[C:30]23)[NH:28]1.[H-].[Na+].Br[CH2:44][CH:45]([CH3:48])[CH2:46][Cl:47]>CN(C)C=O>[Cl:47][CH2:46][CH:45]([CH3:48])[CH2:44][N:28]1[C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([C:30]=23)[S:27]1(=[O:39])=[O:40]

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 690522H-Naphth(1,8-cd)isothiazole 1,1-dioxideHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 14726787HCID 14726787, compoundHCID 15739357HCID 15739357, compound

Product 1

HCID 14726791HCID 14726791, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3- Chloro-2-methylpropyl)naphthol1,8-cd]isothiazole 1,1-dioxide may be prepared in the following manner: the experiment is carried out as in Example 56 for the preparation of 2-(3-bromo-2-hydroxypropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide, starting with naphtho[1,8-cd]isothiazole 1,1-dioxide (10.3 g) in dimethylformamide (125 cc), sodium hydride (2.4 g) in a 50% dispersion in vaseline oil, and 1-bromo-3-chloro-2-methylpropane (5.9 cc). After purification by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and cyclohexane (80-20 vol) as eluant, 2-(3-chloro-2-methylpropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (10.4 g) is obtained, in the form of a green oil, which is used in the crude state in the subsequent syntheses.

Workup

  1. customAfter purification by flash-chromatography on a silica column
  2. additionunder a current of argon at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and cyclohexane (80-20 vol) as eluant

Sources & evidence

ORD record
ord-38454342d33e4cb782e6b1d868967a97
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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