Sodium Hydroxide → HCID 13393424, compound

HRID 615359Notes

Reaction equation

[OH-:1].[NH4+:2].Cl[O-:4].[Na+].[OH-].[Na+].[C:8]([NH:13][C:14]1[CH:23]=[CH:22][C:17]2[N:18]=[C:19]([SH:21])[S:20][C:16]=2[CH:15]=1)(=[O:12])[CH2:9][CH2:10][CH3:11].[Mn]([O-])(=O)(=O)=O.[K+]>O>[C:8]([NH:13][C:14]1[CH:23]=[CH:22][C:17]2[N:18]=[C:19]([S:21]([NH2:2])(=[O:4])=[O:1])[S:20][C:16]=2[CH:15]=1)(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 30 °C

Procedure

To ammonium hydroxide (14.8M) (90 ml) was added dropwise simultaneously sodium hypochlorite solution (5.25%) (42.4 ml) and a solution of sodium hydroxide (1.2 g, 0.03 mole) and 6-butyrylamino-2-mercaptobenzothiazole (7.57 g, 0.03 mole) in H2O (80 ml) with stirring at 5° C. After 1/2 hour the precipitated solid was collected by suction filtration and washed well with cold H2O. The wet solid was suspended in acetone (120 ml) and treated dropwise with 5% aqueous potassium permanganate solution (6.6 g, 0.04 mole in 120 ml H2O) over an hour period maintaining the reaction mixture temperature at 30° C. After stirring for an additional hour, the mixture was treated with decolorizing carbon, then filtered to remove manganese dioxide. Upon acidification of the filtrate with 12 N HCl the solid product precipitated. Crystallization from isopropanol gives 780 mg of 6-butyrylamino-2-benzothiazolesulfonamide, m.p. 246°-247° C.

Workup

filtrationAfter 1/2 hour the precipitated solid was collected by suction filtration
washwashed well with cold H2O
additionthe mixture was treated with decolorizing carbon
filtrationfiltered
customto remove manganese dioxide
customUpon acidification of the filtrate with 12 N HCl the solid product precipitated
customCrystallization from isopropanol

Sources & evidence

ORD record: ord-9716434c6bc34b7cb062144aa7988650
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499103

Reaction notes

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