Benzaldehyde → HCID 19838485, compound

HRID 476755Notes

Reaction equation

HRID 476755 reaction equation
Cl.[NH2:2][CH:3]1[CH2:15][C:14]2[C:6](=[CH:7][C:8]3[CH2:12][CH2:11][O:10][C:9]=3[CH:13]=2)[CH2:5][CH2:4]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1>[CH2:16]([NH:2][CH:3]1[CH2:15][C:14]2[C:6](=[CH:7][C:8]3[CH2:12][CH2:11][O:10][C:9]=3[CH:13]=2)[CH2:5][CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 19838440HCID 19838440, compound

Product 1

HCID 19838485HCID 19838485, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

45 g of the compound of Example 2, 25.4 g of benzaldehyde and 300 ml of benzene are brought to reflux, removing the water formed. The mixture is evaporated to dryness, the residue is taken up with 300 ml of ethanol and 9 g of sodium borohydride are added portionwise, keeping the temperature at approximately 18° C. After one night at room temperature, the ethanol is removed under vacuum and the residue taken up with dilute hydrochloric acid solution. The acid phase is alkalinized and then extracted with ethyl ether. After evaporation of the solvent, the oil obtained is purified on a silica column using a mixture of methylene chloride and methanol (95:5 V/V) as elution solvent.

Workup

  1. temperatureto reflux
  2. customremoving the water
  3. customformed
  4. customThe mixture is evaporated to dryness
  5. additionare added portionwise
  6. customat approximately 18° C
  7. waitAfter one night at room temperature
  8. customthe ethanol is removed under vacuum
  9. extractionextracted with ethyl ether
  10. customAfter evaporation of the solvent
  11. customthe oil obtained
  12. customis purified on a silica column
  13. additiona mixture of methylene chloride and methanol (95:5 V/V)
  14. washas elution solvent

Sources & evidence

ORD record
ord-366b1096f35f453da4c822907905d8d2
Source dataset
uspto-grants-1989_12
Patent number
US04885373

Reaction notes

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