Acetic Acid → 6-Ethylamino-2-benzothiazolesulfonamide
Reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1.[C:17](O)(=O)[CH3:18].[H][H]>O>[CH2:17]([NH:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1)[CH3:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Sodium borohydride (378 mg, 0.01 mole) and 6-amino-2-benzothiazolesulfonamide (459 mg, 0.002 mole) are ground together, then added very slowly over 1 hr. to glacial acetic acid (5 ml.) with stirring under nitrogen at 20° C. After the vigorous evolution of hydrogen has subsided, the reaction mixture is stirred at 20° C. for 3 hrs, treated with H2O, filtered, and made basic with 10N NaOH solution. Neutralization with aqueous HCl followed by extraction with EtOAc and concentration to dryness gives 6-ethylamino-2-benzothiazolesulfonamide. ##STR11## NMR (d6 -DMSO) δ1.21 (3H, t, CH3CH2 --), 3.11 (2H, q, CH3CH2), 3.44 (1H, br s, NH), 6.94 (1H, dd, J=9 Hz, J=3 Hz, Hb), 7.11 (1H, d, J=3 Hz, Hc), 7.79 (1H, d, J=9 Hz), Ha), 8.07 (2H, br s, SO2NH2).
Workup
- additionadded very slowly over 1 hr
- filtrationfiltered
- extractionNeutralization with aqueous HCl followed by extraction with EtOAc and concentration to dryness
Sources & evidence
- ORD record
- ord-4a44eab94c0e4f89aeed023e4e338007
- Source dataset
- uspto-grants-1985_02
- Patent number
- US04499103
Reaction notes
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