2-Chlorobenzaldehyde → HCID 13276668, compound

HRID 620753Notes

Reaction equation

HRID 620753 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([O:16][CH3:17])(=[O:15])[CH2:11][C:12]([CH3:14])=O.Cl.[C:19]([NH2:22])(=[NH:21])[CH3:20].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:11]([C:10]([O:16][CH3:17])=[O:15])=[C:12]([CH3:14])[NH:22][C:19]([CH3:20])=[N:21]1

Participants

6

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 7757Methyl acetoacetateHCID 67170Acetamidine monohydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 13276668HCID 13276668, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.42 g (60 mmols) of 2-chlorobenzaldehyde are boiled with 6.48 ml (60 mmols) of methyl acetoacetate, 6.72 g (60 mmols) of acetamidine HCl and 5.91 g (72 mmols) of anhydrous sodium acetate in 180 ml of ethanol for 18 hours. The mixture is cooled and concentrated. 100 ml of 1N hydrochloric acid and ethyl acetate are added to the resulting evaporation residue and the mixture is shaken thoroughly. The mixture is left to separate, the ethyl acetate phase is extracted by shaking with 100 ml of 1 N hydrochloric acid and the combined aqueous phases are extracted once by shaking with ether and left to separate. The aqueous phase is rendered alkaline with concentrated sodium hydroxide solution and extracted twice by shaking with ethyl acetate. The combined ethyl acetate phases are washed with water, dried and concentrated. The crystalline evaporation residue is recrystallized from acetonitrile. 2.5 g of a slightly yellow substance of melting point 225°-27° C. are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated
  3. addition100 ml of 1N hydrochloric acid and ethyl acetate are added to the resulting evaporation residue
  4. waitThe mixture is left
  5. customto separate
  6. extractionthe ethyl acetate phase is extracted
  7. stirringby shaking with 100 ml of 1 N hydrochloric acid
  8. extractionthe combined aqueous phases are extracted once
  9. stirringby shaking with ether
  10. waitleft
  11. customto separate
  12. extractionextracted twice
  13. stirringby shaking with ethyl acetate
  14. washThe combined ethyl acetate phases are washed with water
  15. customdried
  16. concentrationconcentrated
  17. customThe crystalline evaporation residue is recrystallized from acetonitrile
  18. custom2.5 g of a slightly yellow substance of melting point 225°-27° C. are obtained

Sources & evidence

ORD record
ord-f3890ef2112d4379bf003949668670b2
Source dataset
uspto-grants-1989_04
Patent number
US04822798

Reaction notes

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