Sodium Hydroxide → HCID 13393425, compound

HRID 615361Notes

Reaction equation

[OH-:1].[NH4+:2].Cl[O-:4].[Na+].[OH-].[Na+].[CH2:8]([O:10][C:11]([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])[CH3:9].[Mn]([O-])(=O)(=O)=O.[K+]>O>[CH2:8]([O:10][C:11]([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])[CH3:9]

Participants

Conditions

Temperature: 30 °C

Procedure

To ammonium hydroxide (14.8 M) (215 ml) were added dropwise simultaneously sodium hypochlorite solution (5.25%) (101 ml) and a solution of sodium hydroxide (2.75 g, 0.069 mole) and 6-(N-ethoxycarbonylamino)-2-mercaptobenzothiazole (17.50 g, 0.069 mole) in H2O (187 ml) with stirring at 5° C. After 1/2 hour the precipitated solid was collected by suction filtration and washed well with ice-H2O. The wet solid was suspended in acetone (284 ml) and treated dropwise with a solution of potassium permanganate (15.13 g, 0.092 mole) in H2O (284 ml) over an hour period maintaining the reaction temperature at 30° C. After stirring for an additional hour, the mixture was filtered to remove manganese dioxide, and the filtrate acidified with 12N HCl to precipitate the solid product. Chromatography on a silica gel column eluting with EtOAc:hexane (50:50 v/v) followed by crystallization from ethanol gave 500 mg of 6-(N-ethoxycarbonylamino)-2-benzothiazolesulfonamide, m.p. 223°- 224° C.

Workup

filtrationAfter 1/2 hour the precipitated solid was collected by suction filtration
washwashed well with ice-H2O
filtrationthe mixture was filtered
customto remove manganese dioxide
customto precipitate the solid product
washChromatography on a silica gel column eluting with EtOAc:hexane (50:50 v/v)
customfollowed by crystallization from ethanol

Sources & evidence

ORD record: ord-de8d633fe8c04856830f57cdee5c9767
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499103

Reaction notes

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