Ammonium Hydroxide → Ethoxzolamide
Reaction equation
[OH-:1].[NH4+:2].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[CH:7]=1)[CH3:4].[O-:16]Cl.[Na+]>[OH-].[Na+]>[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([S:13]([NH2:2])(=[O:16])=[O:1])[S:12][C:8]=2[CH:7]=1)[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of ammonium hydroxide (650 mL) was cooled to 0° C. in an ice/methanol bath. A solution containing 6-ethoxy-2-mercapto-benzothiazole (16.0 g, 0.076 mol) in 170 mL of 5% NaOH and a solution of 5.25% NaOCl (150 mL) were added simultaneously to the ammonium hydroxide solution while maintaining a temperature of 0° C. The reaction was stirred for 15 min. upon completing the addition, and the sulfenamide was collected by vacuum filtration. The sulfenamide was dissolved in 1 L of acetone and oxidized by the addition of 450 mL of 5% KMn04 over 4 hours. The MnO2 was removed by filtering through Celite, and the acetone was removed under vacuum. The product was precipitated from solution by acidification with concentrated HCl to yield 11.7 g (59.7%) of 6-ethoxy-2-benzothiazolesulfonamide, which was purified by dissolving it in 5% NaOH, filtering, and precipitating with concentrated HCl; mp 190°-191° C.; MS, m/e 258 (M,calcd 258).
Workup
- additionthe addition
- filtrationthe sulfenamide was collected by vacuum filtration
- dissolutionThe sulfenamide was dissolved in 1 L of acetone
- additionoxidized by the addition of 450 mL of 5% KMn04 over 4 hours
- customThe MnO2 was removed
- filtrationby filtering through Celite
- customthe acetone was removed under vacuum
- customThe product was precipitated from solution by acidification with concentrated HCl
Sources & evidence
- ORD record
- ord-724d7f35a98b4fadb472c61d618182eb
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05059613
Reaction notes
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