Sodium Methoxide → HCID 70632913, compound

HRID 597455Notes

Reaction equation

HRID 597455 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[NH:7][C:8](=[O:13])/[CH:9]=[C:10](\Cl)/[CH3:11])(=[O:3])[CH3:2].[CH3:17][O-:18].[Na+]>CO>[C:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[NH:7][C:8](=[O:13])/[CH:9]=[C:10](\[O:18][CH3:17])/[CH3:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86734581HCID 86734581, compound

Product 1

HCID 70632913HCID 70632913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 400 ml of methanol, 41 g of m-acetyl-3-chlorocrotonanilide and 9.4 g of sodium methylate was stirred at 20° C for 72 hours and the mixture was vacuum filtered to recover the sodium chloride formed and the desired product. The solid was dissolved in refluxing acetone and the mixture was filtered. The filtrate was evaporated to dryness under reduced pressure. The waste waters were evaporated to dryness and the residue was taken up in 200 ml of a 7-3 benzene-ethyl acetate mixture. The mixture was vacuum filtered and the solid was dissolved in refluxing acetone. The solution was filtered and the filtrate was evaporated to dryness for a total yield of 19.5 g of m-acetyl-3-methoxy-crotonanilide melting at 168° C.

Workup

  1. filtrationfiltered
  2. customto recover the sodium chloride
  3. customformed

Sources & evidence

ORD record
ord-1eda944ee0604d35ab1a055c214adade
Source dataset
uspto-grants-1977_03
Patent number
US04014679

Reaction notes

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