Ethyl Acetate → N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

HRID 2360496Notes

Reaction equation

HRID 2360496 reaction equation
Cl.[NH2:2][C:3]1[C:4]([O:18][CH3:19])=[C:5]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:6]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1.C(OCC)(=O)C.[OH-].[Na+]>O>[NH2:2][C:3]1[C:4]([O:18][CH3:19])=[C:5]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:6]=[C:7]([C:9]([CH3:11])([CH3:12])[CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21079205N-(3-amino-5-tert-butyl-2-methoxyphenyl)methanesulphonamide-hydrochloride

Product 1

HCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulphonamid hydrochloride (J. Med. Chem. 2007, 50 (17), 4016-26) are suspended in 200 ml of water and 600 ml of ethyl acetate and sufficient 4 N sodium hydroxide solution is added with vigorous stirring to give a pH of 11. Then the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are dried on magnesium sulphate and evaporated down in vacuo. The solid thus obtained is further reacted directly.

Workup

  1. customto give a pH of 11
  2. customThen the phases are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. customthe combined organic phases are dried on magnesium sulphate
  5. customevaporated down in vacuo
  6. customThe solid thus obtained
  7. customis further reacted directly

Sources & evidence

ORD record
ord-a6b51654935e421b8b2662d4306367fe
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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