1,3-Dibromo-2-propanol → HCID 19830860, compound

HRID 1493282Notes

Reaction equation

HRID 1493282 reaction equation
Br[C:2]1[C:11]2[NH:12][S:13](=O)(=O)[C:9]3[C:10]=2[C:5]([CH:6]=[CH:7][CH:8]=3)=[CH:4][C:3]=1CC(O)C.[H-].[Na+].[Br:22][CH2:23][CH:24]([OH:27])[CH2:25]Br>CN(C)C=O>[Br:22][CH2:23][CH:24]([OH:27])[CH2:25][N:12]1[C:11]2[CH:2]=[CH:3][CH:4]=[C:5]3[CH:6]=[CH:7][CH:8]=[C:9]([C:10]=23)[S:13]1

Participants

5

Reactant 3

HCID 72871,3-Dibromo-2-propanolHCID 24758Sodium hydrideHCID 86744823HCID 86744823, compound

Product 1

HCID 19830860HCID 19830860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

2-(3-Bromo-2-hydroxypropylnaphtho[1,8-cd]isothiazole 1,1-dioxide may be prepared in the following manner: a solution of naphtho[18-cd]isothiazole 1,1-dioxide (41 g) in dimethylformamde (1000 cc) is added over 2 hours under a current of argon to a suspension of sodium hydride (9.6 g) in a 50% dispersion in vaseline oil in dimethylformamide (100 cc), maintaining the temperature between 20 and 35° C. The reaction medium is stirred for 30 minutes at a temperature of about 20° C., then 1,3-dibromo-2-hydroxypropane (20.5 cc) in dimethylformamide (500 cc) is added over 10 minutes. Stirring is maintained for 15 hours at a temperature of about 20° C. The reaction mixture is concentrated to dryness at 70° C under reduced pressure (0.5 mm Hg; 0.07 kPa). The residue is purified by chromatography on a silica column, under a current of argon with a mixture of dichloromethane and methanol (95-5 vol) as eluant. 2-(3-Bromo-2-hydroxypropyl)naphtho[1,8-cd]isothiazole 1, -dioxide (62.1 g) is obtained, in the form of a green oil which is used in the crude state in the subsequent synthesis.

Workup

  1. temperaturemaintaining the temperature between 20 and 35° C
  2. stirringStirring
  3. temperatureis maintained for 15 hours at a temperature of about 20° C
  4. concentrationThe reaction mixture is concentrated to dryness at 70° C under reduced pressure (0.5 mm Hg; 0.07 kPa)
  5. customThe residue is purified by chromatography on a silica column
  6. additionunder a current of argon with a mixture of dichloromethane and methanol (95-5 vol) as eluant

Sources & evidence

ORD record
ord-93e9de8a20aa42c7907596d537bcd0cd
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

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