Hydrochloric Acid → 2-amino-N-(methylsulfonyl)benzamide

HRID 49417Notes

Reaction equation

HRID 49417 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[Li].[C:7]12[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:12]C(=O)O[C:8]2=[O:9].Cl>CS(C)=O.C(OCC)C>[CH3:1][S:2]([NH:5][C:8]([C:7]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:12])=[O:9])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 86584665Lithium methanesulfonamidate

Product 1

HCID 234341902-amino-N-(methylsulfonyl)benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

Lithium methanesulfonamidate (1.0 g, 10 mmol) and isatoic anhydride (1.63 g, 10 mmol) in dimethyl sulfoxide (5 mL) were heated at 80° C. for 30 min. The reaction was cooled down to room temperature and acidified with hydrogen chloride in diethyl ether. The ether was evaporated and water added. The precipitated oil was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (95:5). The desired material was obtained in a yield of 0.52 g.

Workup

  1. customThe ether was evaporated
  2. additionwater added
  3. customThe precipitated oil was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (95:5)

Sources & evidence

ORD record
ord-d20b327c0978445a802449c0ed13dd3e
Source dataset
uspto-grants-2004_03
Patent number
US06706749B2

Reaction notes

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