Sodium Acetate → 2-Acetoxy-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfony-2-phenylacetamide

HRID 1451162Notes

Reaction equation

HRID 1451162 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].[C:26]([O-:29])(=[O:28])[CH3:27].[Na+]>C(O)(=O)C>[C:26]([O:29][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])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 199739322-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide

Product 1

HCID 677141702-Acetoxy-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfony-2-phenylacetamideYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide (0.5 g) and anhydrous sodium acetate (0.25 g) were refluxed in glacial acetic acid (10 ml) for 7 hours. The acetic acid was evaporated off under vacuum, and the residue was taken into ether. The ether solution was washed with water (3 times), dried over magnesium sulfate, and evaporated under vacuum to give 0.52 g of a brown glass. Trituration with diisopropyl ether gave an off-white solid, which was filtered off, washed with diisopropyl ether and dried to give 0.3 g of the desired product, mp 141°-143° C.

Workup

  1. customThe acetic acid was evaporated off under vacuum
  2. washThe ether solution was washed with water (3 times)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-5db6ada7970a4ff68736fef82eeba95f
Source dataset
uspto-grants-1997_02
Patent number
US05604181

Reaction notes

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