Sodium Bicarbonate → 4-Hydroxy-7-[2-[[3-[[2-(2-phenylethoxy)ethyl]sulfonyl]propyl]amino]ethyl]-2(3H)-benzothiazolone

HRID 265302Notes

Reaction equation

HRID 265302 reaction equation
Cl.[OH:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[C:6]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][S:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:21])=[O:20])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>>[OH:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[C:6]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][S:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)(=[O:21])=[O:20])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 67614902HCID 67614902, compound

Product 1

HCID 99561014-Hydroxy-7-[2-[[3-[[2-(2-phenylethoxy)ethyl]sulfonyl]propyl]amino]ethyl]-2(3H)-benzothiazoloneYield 92.9%

Procedure

An aqueous solution (500 ml) of the title compound from Example 20 (4.9 g) was mixed with an excess of aqueous sodium hydrogen carbonate. The free base was extracted with chloroform and the combined extracts were washed with water and dried (MgSO4), filtered and the chloroform removed under reduced pressure to yield the subtitled compound as an off-white solid (4.22 g, 91%).

Workup

  1. extractionThe free base was extracted with chloroform
  2. washthe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe chloroform removed under reduced pressure

Sources & evidence

ORD record
ord-d9d6f7dd97084169ad53d23c9ae7ea54
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

Loading…