Benzaldehyde → HCID 178469930, compound

HRID 2295363Notes

Reaction equation

HRID 2295363 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][NH:12][N:11]=1>C1(C)C=CC=CC=1>[CH2:1]([NH:9][C:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][NH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 178469928HCID 178469928, compound

Product 1

HCID 178469930HCID 178469930, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

21.2 g of benzaldehyde is added to a suspension of 25 g of 3-amino-4-ethoxycarbonylpyrazole in 200 ml of toluene. The whole is boiled while separating water. In 3 hours a total of 5 ml of water collects. After the toluene has been evaporated, 50 ml of methanol and 50 ml of THF are added and, under cooling, 23 g of NaBH4 is added at 0°-5° C. After 4 hours' at room temperature, the solvent mixture is drawn off; then 200 ml of ice water is added the whole is extracted three times with 150 ml of methylene chloride each time and the extract is dried over Na2SO4. After concentration, an oil remains that is recrystallized from ligroin/toluene; m.p. 99°-100° C.

Workup

  1. customwhile separating water
  2. customAfter the toluene has been evaporated
  3. addition50 ml of methanol and 50 ml of THF are added
  4. temperatureunder cooling
  5. addition23 g of NaBH4 is added at 0°-5° C
  6. waitAfter 4 hours' at room temperature
  7. additionthen 200 ml of ice water is added the whole
  8. extractionis extracted three times with 150 ml of methylene chloride each time
  9. dry with materialthe extract is dried over Na2SO4
  10. concentrationAfter concentration
  11. customthat is recrystallized from ligroin/toluene

Sources & evidence

ORD record
ord-50151eb3cdc4455890a3ab840b72bbd6
Source dataset
uspto-grants-1984_01
Patent number
US04424363

Reaction notes

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