Formaldehyde → HCID 20248791, compound

HRID 1285303Notes

Reaction equation

HRID 1285303 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[CH:6][NH:5][CH:4]=1)#[N:2].C=[O:17].[N+](=C1CCCCC2C1CCCC=2)=[N-].[CH2:31]([O:33]CC(Cl)=O)C.[O:38]1[CH2:42]C[CH2:40][CH2:39]1>C(N(CC)CC)C>[CH3:31][O:33][CH2:40][C:39]([O:38][CH2:42][N:5]1[CH:4]=[C:3]([C:1]#[N:2])[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[CH:6]1)=[O:17]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 84189Ethoxyacetyl chlorideHCID 91724FenpiclonilHCID 22747271HCID 22747271, compound

Product 1

HCID 20248791HCID 20248791, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4.5 g of 3-cyano-4-(2,3-dichlorophenyl)pyrrole are dissolved in 50 ml of tetrahydrofuran and to the solution are added 0.65 g of paraformaldehyde, 3.0 ml of triethylamine and 0.5 ml of diazobicyclo[5.4.0]undec-7-ene. The mixture is stirred for 2 hours at room temperature to form a clear solution. With stirring, 2.0 ml of ethoxyacetyl chloride are slowly added dropwise at 5° C. The reaction mixture is kept for 21/2 hours at 0°-5° C. and then filtered. The filtrate is concentrated and the residue is crystallised from ether/petroleum ether to give colourless crystals of the title compound with a melting point of 72°-75° C.

Workup

  1. customto form a clear solution
  2. stirringWith stirring
  3. custom2 hours
  4. customat 0°-5° C.
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-0b4a0d0b967247aa987a50be45c396f7
Source dataset
uspto-grants-1986_01
Patent number
US04567052

Reaction notes

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