Formaldehyde → HCID 20312937, compound

HRID 2420081Notes

Reaction equation

HRID 2420081 reaction equation
C=O.[Cl:3][C:4]1[CH:5]=[C:6]([N:11]2[CH2:16][CH2:15][O:14][NH:13][C:12]2=[O:17])[CH:7]=[CH:8][C:9]=1[Cl:10].[C:18]([O-])(=[O:20])C.[Na+]>O1CCOCC1>[OH:20][CH2:18][N:13]1[C:12](=[O:17])[N:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)[CH2:16][CH2:15][O:14]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 20312935HCID 20312935, compound

Product 1

HCID 20312937HCID 20312937, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

300 ml of an aqueous solution of 30% formic aldehyde were added to a mixture of 30 g of 4-(3',4'-dichlorophenyl)-3-oxo-5,6-dihydro-1,2,4-oxadiazine, 30 g of anhydrous sodium acetate and 300 ml of dioxane and then the mixture was stirred for 2 hours at 20°-25° C and was acidified. The mixture was extracted with ethyl acetate and the extracts were dried and evaporated to dryness under reduced pressure. The residue was taken up in isopropyl ether and the mixture was vacuum filtered. The recovered solids were dried to obtain 30 g of 2-hydroxymethyl-4-(3',4'-dichlorophenyl)-3-oxo-5,6-dihydro-1,2,4-oxadiazine melting at 134° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe extracts were dried
  3. customevaporated to dryness under reduced pressure
  4. filtrationfiltered
  5. customThe recovered solids were dried

Sources & evidence

ORD record
ord-71f1ed81cd114e3e9e1c2ac4adc355e1
Source dataset
uspto-grants-1978_08
Patent number
US04108993

Reaction notes

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