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

HRID 2121734Notes

Reaction equation

HRID 2121734 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-f86a31ee3e934ef2b80d13a6a8072894
Source dataset
uspto-grants-2004_02
Patent number
US06696475B2

Reaction notes

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