Formaldehyde → HCID 19844955, compound

HRID 2351941Notes

Reaction equation

HRID 2351941 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.Cl.[CH3:20]NC.C=O>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH2:20])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 198449561,3-Bis(4-fluorophenyl)propan-1-one

Product 1

HCID 19844955HCID 19844955, compound

Procedure

59.4 g of 4,4'-difluoro-β-phenylpropiophenone, prepared in accordance with step (a), together with 39.2 g of dimethylamine hydrochloride and 14.4 g of paraformaldehyde are heated overnight under reflux. The reaction mixture is then concentrated by evaporation and the residue is taken up in 300 ml of water and is extracted with three 200 ml portions of ether. The combined ether extracts are washed twice with water and then twice with a saturated solution of NaCl, dried over Na2SO4 and filtered. The filtrate is concentrated, affording 1-(4-fluorophenyl)-2-(4-fluorobenzyl)-prop-2-en-1-one of the formula ##STR9## as a crude product which is immediately reacted further. The crude product is dissolved in 140 ml of ethanol and a solution of 18.8 g of hydrazine hydrate in 70 ml of methanol is added dropwise to this ethanolic solution. When the addition is complete, the reaction mixture is heated under reflux for three hours, cooled and then concentrated by rotary evaporation. The resultant residue is taken up in ether and the ethereal solution is washed twice with water and then twice with a saturated solution of NaCl, dried over Na2SO4 and filtered. The filtrate is concentrated by evaporation, thus affording the title compound of the formula ##STR10##

Workup

  1. temperatureare heated overnight
  2. temperatureunder reflux
  3. concentrationThe reaction mixture is then concentrated by evaporation
  4. extractionis extracted with three 200 ml portions of ether
  5. washThe combined ether extracts are washed twice with water
  6. dry with materialtwice with a saturated solution of NaCl, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-129e82a1438543b186b10454c5022561
Source dataset
uspto-grants-1989_10
Patent number
US04874778

Reaction notes

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