Water → 3-Amino-6-chloro-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

HRID 1024571Notes

Reaction equation

[CH2:1]([N:3]([O:21][CH3:22])[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])[CH3:2].S(=O)(=O)(O)O.O>O1CCOCC1>[NH2:12][C:11]1[C:15]([OH:14])=[C:7]([S:4]([N:3]([O:21][CH3:22])[CH2:1][CH3:2])(=[O:6])=[O:5])[C:8]([Cl:20])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-tert-Butyl-6-chloro-benzooxazole-7-sulfonic acid ethyl-methoxy-amide (2.7 g, 7.78 mmol) in dioxane (15 ml) was treated with a mixture of concentrated sulphuric acid (3.5 ml) and water (3.5 ml). The reaction mixture was heated at 80° C. for a total of 8 h and then allowed to cool to RT. Dioxane was removed in vacuo and the resulting aqueous mixture was treated with 1M NaOH (aq) until pH7 was attained. The reaction mixture was extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to afford the title compound as a brown solid; [M+H]+ 281.1.

Workup

temperatureto cool to RT
customDioxane was removed in vacuo
additionthe resulting aqueous mixture was treated with 1M NaOH (aq) until pH7
extractionThe reaction mixture was extracted with EtOAc
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9a724d3ff7104b5cbe39a9bd39be7cae
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722925B2

Reaction notes

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