Methanesulfonamide sodium salt → 2-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide

HRID 1451159Notes

Reaction equation

HRID 1451159 reaction equation
[Cl:1][C:2]([C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[Na+].[CH3:23][S:24]([NH-:27])(=[O:26])=[O:25]>O1CCCC1>[Cl:1][C:2]([C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH:27][S:24]([CH3:23])(=[O:26])=[O:25])=[O:4]

Participants

4

Reactant 2

HCID 13150714Methanesulfonamide sodium saltHCID 199739422-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-2phenylacetyl chloride

Product 1

HCID 199739322-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamideYield 62.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Stage (b) (3.1 g) in dry tetrahydrofuran (10 ml) was added dropwise to stirred, cooled (5° C.) methanesulfonamide sodium salt (2.8 g) in dry tetrahydrofuran (25 ml). Stirring was continued until most solid had dissolved (2 hours) and the reaction mixture was allowed to stand at room temperature overnight. The solvent was then evaporated off under vacuum and the residue was treated with ether. The precipitated solid was taken up in aqueous potassium bicarbonate, the ether solution extracted again with bicarbonate and then with water. The combined aqueous phases were washed with ether, fresh ether was then added and the whole was acidified to pH=1 with hydrochloric acid as quickly as possible with stirring. The ether solution was separated, and the aqueous phase was extracted twice more. The combined ether solutions were washed with water (5 times), dried over magnesium sulfate and evaporated under vacuum to give 2.3 g of the desired product. Washing with a small volume of diisopropyl ether gave 1.95 g of pure product as a viscous liquid.

Workup

  1. stirringStirring
  2. dissolutionhad dissolved (2 hours)
  3. customThe solvent was then evaporated off under vacuum
  4. additionthe residue was treated with ether
  5. extractionthe ether solution extracted again with bicarbonate
  6. washThe combined aqueous phases were washed with ether, fresh ether
  7. additionwas then added
  8. stirringwith stirring
  9. customThe ether solution was separated
  10. extractionthe aqueous phase was extracted twice more
  11. washThe combined ether solutions were washed with water (5 times)
  12. dry with materialdried over magnesium sulfate
  13. customevaporated under vacuum

Sources & evidence

ORD record
ord-263703842c994aafaffa79266b77c8cf
Source dataset
uspto-grants-1997_02
Patent number
US05604181

Reaction notes

Loading…