Benzaldehyde → HCID 22414827, compound

HRID 1721420Notes

Reaction equation

HRID 1721420 reaction equation
C1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH3:16])[CH:11]=[CH:10][C:9]=1[CH3:17].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([BH3-])#N.[Na+]>O>[CH2:18]([NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH3:16])[CH:11]=[CH:10][C:9]=1[CH3:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 241BenzeneHCID 5003444Sodium cyanoborohydrideHCID 233697555-Ethoxy-2-methylaniline

Product 1

HCID 22414827HCID 22414827, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of benzene was added to 20.8 g (138 mmol) of 2-amino-4-ethoxytoluene and 17.8 g (168 mmol) of benzaldehyde, and the mixture was heated with refluxing for 5 hours in a reaction vessel equipped with a water separator. After cooling, the reaction solution was concentrated under reduced pressure. 640 ml of methanol was added to the residue, followed by the addition of acetic acid to adjust pH to 5. To this was added 13.1 g (208 mmol) of sodium cyanoborohydride while stirring under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, purified by column chromatography (silica gel, chloroform), and recrystallized (chloroform-n-hexane) to obtain 19.7 g (yield, 59.2%) of colorless prisms of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith refluxing for 5 hours in a reaction vessel
  3. temperatureAfter cooling
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. addition640 ml of methanol was added to the residue
  6. additionfollowed by the addition of acetic acid
  7. temperatureunder cooling with ice
  8. stirringthe mixture was stirred overnight at room temperature
  9. concentrationThe reaction mixture was concentrated
  10. custompurified by column chromatography (silica gel, chloroform)
  11. customrecrystallized (chloroform-n-hexane)
  12. customto obtain

Sources & evidence

ORD record
ord-f649f13e6d204d9390fe1a251f919559
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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