Ethyl Acrylate → HCID 14840397, compound

HRID 979505Notes

Reaction equation

HRID 979505 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH2:17])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O-]CC.[Na+].[C:22](OCC)(=[O:25])[CH:23]=[CH2:24]>CCO.C1(C)C=CC=CC=1>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:24][CH2:23][C:22](=[O:25])[NH:17]2)=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 2723922Sodium ethoxideHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Product 1

HCID 14840397HCID 14840397, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 2.5 g of 4-benzyloxyphenylhydrazine HCl and sodium ethoxide (1.6 g) in 10 ml of EtOH and 10 ml of toluene are added 1.08 of ethyl acrylate at room temperature. The reaction mixture is then heated at 85° C. overnight. The reaction mixture is evaporated to dryness under vacuum and water added to the residue and the pH adjusted to pH 6 by 1N-HCl solution. Extraction with ethyl acetate and drying the organic solution and evaporating to dryness yields 2.8 g of crude product. Purification by dry column chromatography gives 0.3 g of product; mp. 130°-134° C.

Workup

  1. customThe reaction mixture is evaporated to dryness under vacuum and water
  2. additionadded to the residue
  3. extractionExtraction with ethyl acetate
  4. customdrying the organic solution
  5. customevaporating to dryness
  6. customyields 2.8 g of crude product
  7. customPurification
  8. customby dry column chromatography

Sources & evidence

ORD record
ord-593bbc148baa4e09a405aabdd846d79e
Source dataset
uspto-grants-1987_05
Patent number
US04668694

Reaction notes

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