Acetic Acid → Ethyl 5-amino-1,2-benzisothiazole-3-acetate

HRID 277378Notes

Reaction equation

C(O)(=O)C.[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]=2[CH:22]=1)([O-])=O.C(=O)([O-])O.[Na+].C(Cl)Cl>C(OCC)(=O)C.[Fe]>[NH2:5][C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]=2[CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 10% acetic acid solution (31.0 mL) is stirred at 50° C., treated with iron powder (0.656 g), treated dropwise with a solution of ethyl 5-nitro-1,2-benzisothiazole-3-acetate (1.03 g, 3.88 mmol) in ethyl acetate, stirred at 50° C. for two hours, treated with additional iron powder (0.305 g), stirred at 50° C. for 15 minutes, and poured into saturated sodium hydrogen carbonate solution. The resultant aqueous mixture is extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and methylene chloride gives the title product as a yellow oil.

Workup

stirringstirred at 50° C. for 15 minutes
extractionThe resultant aqueous mixture is extracted with ethyl acetate
washThe combined organic extracts are washed sequentially with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto obtain an oil

Sources & evidence

ORD record: ord-dc6081b8c3a64c8bac0128b9437fcd1c
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355796B1

Reaction notes

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