Sodium Methoxide → 2-(4,6-Dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2methoxy-2-phenylacetamid

HRID 1451161Notes

Reaction equation

HRID 1451161 reaction equation
Cl[C:2]([C:16]1[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([NH:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:4].[CH3:26][O-:27].[Na+]>CO>[CH3:25][O:24][C:18]1[CH:19]=[C:20]([O:22][CH3:23])[N:21]=[C:16]([C:2]([O:27][CH3:26])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([NH:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:4])[N:17]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 199739322-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide

Product 1

HCID 199739432-(4,6-Dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2methoxy-2-phenylacetamidYield 67.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide (0.7 g) was boiled under reflux with sodium methoxide (0.2 g) in methanol (30 ml) for 5 hours. The methanol was evaporated off under vacuum. The residue was treated with ether and the precipitated sodium salt was taken into water. The aqueous solution was washed with ether, fresh ether was added, and the whole was acidified with hydrochloric acid. A white solid crystallised from the ether layer. This was filtered off, washed with water and a little ether, and dried to give 0.47 g of the desired product, mp 155°-7° C.

Workup

  1. customThe methanol was evaporated off under vacuum
  2. additionThe residue was treated with ether
  3. washThe aqueous solution was washed with ether, fresh ether
  4. additionwas added
  5. customA white solid crystallised from the ether layer
  6. filtrationThis was filtered off
  7. washwashed with water
  8. dry with materiala little ether, and dried

Sources & evidence

ORD record
ord-71928bfd14d94f979fb9f379a4ad5cfd
Source dataset
uspto-grants-1997_02
Patent number
US05604181

Reaction notes

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