Acetic Acid → 6-(1-Methylethyl)amino-2-benzothiazolesulfonamide

HRID 615358Notes

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(O)(=O)C.[H][H].[CH3:23][C:24]([CH3:26])=O>O>[CH3:23][CH:24]([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)[CH3:26]

Participants

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 to a mixture of glacial acetic acid (5 ml) and acetone (5 ml) with stirring under nitrogen at 20° C. After vigorous evolution of hydrogen, the reaction mixture is stirred at 20° C. for 2 hrs, treated with H2O, filtered, made basic with 10N NaOH solution, then neutralized with aqueous HCl to give 6-(1-methylethyl)amino-2-benzothiazolesulfonamide.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-c8e9362002e14e7c993cd60ddd4fbaf9
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499103

Reaction notes

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