Formaldehyde → HCID 13235877, compound

HRID 649133Notes

Reaction equation

HRID 649133 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]=[O:16].S(Cl)([Cl:19])=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:15](=[O:16])[N:12]([CH2:11][Cl:19])[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24386Thionyl ChlorideHCID 128816476-(3-Bromophenyl)pyridazin-3(2H)-one

Product 1

HCID 13235877HCID 13235877, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 50 ml of dry benzene were added 2.51 g of 6-(3-bromophenyl)-3(2H)-pyridazinone, 0.45 g of paraformaldehyde and 1 ml of thionyl chloride, after which the mixture was heated under reflux for 1 hour. The mixture was then cooled and filtered, and the filtrate was evaporated to dryness under reduced pressure, to give 3.11 g of crude crystals of the desired Compound No. 5. These were recrystallised from a 4:1 by volume mixture of hexane and benzene, to give 2.0 g of pure Compound No. 5, in the form of white needles melting at 135°-137° C.

Workup

  1. temperatureafter which the mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. customto give 3.11 g of crude crystals of the desired Compound No
  7. customThese were recrystallised from a 4:1 by volume mixture of hexane and benzene

Sources & evidence

ORD record
ord-05aba5faa75549909a066ee6b8a41917
Source dataset
uspto-grants-1988_04
Patent number
US04738961

Reaction notes

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