Formaldehyde → HCID 13102610, compound

HRID 648108Notes

Reaction equation

HRID 648108 reaction equation
N1CCCCC1.C=O.[F:9][CH:10]([F:28])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH2:20])=[CH:14][CH:13]=1.O.[NH2:30][NH2:31]>C(O)C.CO.C(O)(=O)C>[F:9][CH:10]([F:28])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:20][NH:31][N:30]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 24654Hydrazine hydrate (1:1)HCID 13102609HCID 13102609, compound

Product 1

HCID 13102610HCID 13102610, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

17.5 g. of crude Compound No. 10 obtained by Example 3 was added to a mixture comprising 0.9 ml. of piperidine, 0.9 ml. of acetic acid, 25 ml. of 37% formaline and 180 ml. of methyl alcohol, and the mixture was refluxed and reacted for 3 hours. The reaction mixture was concentrated under reduced pressure, and then 150 ml. of water and 200 ml. of chloroform were added thereto for liquid phase separation, whereupon an organic phase was obtained. The organic phase was dried over anhydrous sodium sulfate and chloroform was distilled off to obtain 18.0 g. of 4'-difluoromethoxy-2-phenylacrylophenone (ND20 :1.5819). Then, 17.5 g. of this product and 8 ml. of hydrazine hydrate were refluxed in ethyl alcohol for reaction for 3 hours. After the reaction, the reaction mixture was concentrated under reduced pressure, and 80 ml. of water and 100 ml. of chloroform were added, whereupon an organic phase was obtained. After drying the organic phase over anhydrous sodium sulfate, chloroform was distilled off, whereupon 17.5 g. of 3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline (melting point: 65°-75° C.) was obtained. Then, 5.8 g. of the compound thus obtained and 3.1 g. of 4-chlorophenylisocyanate were added to dried ethyl ether and reacted for 6 hours under reflux. After cooling the reaction mixture, precipitated crystals were collected by filtration, whereby 5.3 g. of the product was obtained. This product was confirmed by the NMR spectrum to be 1-(4-chlorophenyl-carbamoyl)-3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline. (Melting point: 147.0°-148.0° C.).

Workup

  1. custom10 obtained by Example 3
  2. additionwas added to a mixture comprising 0.9 ml
  3. customreacted for 3 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionof chloroform were added
  6. customfor liquid phase separation
  7. customwhereupon an organic phase was obtained
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate and chloroform
  9. distillationwas distilled off
  10. customto obtain 18.0 g
  11. customAfter the reaction
  12. concentrationthe reaction mixture was concentrated under reduced pressure, and 80 ml
  13. additionof chloroform were added, whereupon an organic phase
  14. customwas obtained
  15. dry with materialAfter drying the organic phase over anhydrous sodium sulfate, chloroform
  16. distillationwas distilled off, whereupon 17.5 g

Sources & evidence

ORD record
ord-5f6116afb6274dc8ae67dee701414f76
Source dataset
uspto-grants-1983_10
Patent number
US04410732

Reaction notes

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