Formaldehyde → HCID 20322577, compound

HRID 840004Notes

Reaction equation

HRID 840004 reaction equation
[CH2:1]([C:3]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH3:11])[C:6]2=[O:12])[CH:4]1[CH3:19])[CH3:2].C=O.[C:23](=O)([O-])O.[Na+]>C(O)=O>[CH2:1]([C:3]1([CH3:20])[N:15]([CH3:23])[C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH3:11])[C:6]2=[O:12])[CH:4]1[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 203224527,9-Diethyl-3,6,7,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione2×

Product 1

HCID 20322577HCID 20322577, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 5.5 g of the 7,9-diethyl-3,6,7,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (Compound 2) obtained in Example 2 were added 1.8 g of formic acid and 6.3 g of 37% formalin; the mixture was stirred at room temperature for one hour and then refluxed by heating for 5 hours. After cooling the reaction mixture, its pH was adjusted to a value of 8 by addition of a 5% aqueous solution of sodium hydrogen carbonate; the solution was then extracted with ethyl acetate. The extract was dried over potassium carbonate and the solvent was then removed. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate) to give 5.58 g of Compound 64, mp 190° - 195° C.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 5 hours
  3. temperatureAfter cooling the reaction mixture, its pH
  4. extractionthe solution was then extracted with ethyl acetate
  5. dry with materialThe extract was dried over potassium carbonate
  6. customthe solvent was then removed
  7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-f6363b8d714f43fba639f42472c6401f
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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