Sulfuric Acid → 3-Amino-6-chloro-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

HRID 1024562Notes

Reaction equation

[CH3:1][O:2][N:3]([CH3:21])[S:4]([C:7]1[C:15]2[O:14]C(C(C)(C)C)=[N:12][C:11]=2[CH:10]=[CH:9][C:8]=1[Cl:20])(=[O:6])=[O:5].S(=O)(=O)(O)O>O1CCOCC1.O>[NH2:12][C:11]1[C:15]([OH:14])=[C:7]([S:4]([N:3]([O:2][CH3:1])[CH3:21])(=[O:6])=[O:5])[C:8]([Cl:20])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 30 °C

Procedure

2-tert-Butyl-6-chloro-benzooxazole-7-sulfonic acid methoxy-methyl-amide (4.8 g, 14.42 mmol) in dioxane (55 ml) and water (20 ml) was treated with concentrated sulphuric acid (20 ml) added dropwise over 30 minutes maintaining the temperature<30° C. The reaction mixture was heated at reflux for 2.5 h and then allowed to cool to RT. Dioxane was removed in vacuo and the resulting aqueous residue was basified with sat. NaHCO3 solution (250 ml) to pH12. The reaction mixture was extracted with EtOAc (3×200 ml) and the combined organic extracts were washed with water (3×100 ml) sat. brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound as a brown solid; [M+H]+ 266.

Workup

additionadded dropwise over 30 minutes
temperatureThe reaction mixture was heated
temperatureat reflux for 2.5 h
temperatureto cool to RT
customDioxane was removed in vacuo
extractionThe reaction mixture was extracted with EtOAc (3×200 ml)
washthe combined organic extracts were washed with water (3×100 ml) sat. brine (100 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8cf1670a0424470eafc8c92bad5043b4
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722925B2

Reaction notes

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