Formic Acid → HCID 21545501, compound

HRID 268227Notes

Reaction equation

HRID 268227 reaction equation
[CH:1](O)=O.[C:4]([N:12]1[CH2:17][CH:16]2[CH2:18][CH2:19][CH:13]1[CH2:14][NH:15]2)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C=O>>[C:4]([N:12]1[CH2:17][CH:16]2[CH2:18][CH2:19][CH:13]1[CH2:14][N:15]2[CH3:1])(=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 21545508HCID 21545508, compound

Product 1

HCID 21545501HCID 21545501, compoundYield 100.3%

Conditions

Temperature
0 °C

Procedure

To 7.4 ml of 88% formic acid (0.17 mole) was added 14.6 g (0.0675 mole) of 2-benzoyl-2,5-diazabicyclo[2.2.2]octane with stirring at 0°C. A 36% aqueous solution of formaldehyde (6.0 ml, 0.078 mole) was added, and, after visible gas evolution had ceased, the mixture was heated at 80°C until renewed gas evolution has stopped (1 hour). After 3 hours at 90°-100°C, volatiles were removed in vacuo. The residue was dissolved in water, made alkaline with 20% aqueous sodium hydroxide, and extracted with chloroform. After drying with sodium sulfate, the extracts yielded 15.6 g (100%) of colorless oily 2-benzoyl- 5-methyl-2,5-diazabicyclo[2.2.2]octane that was homogeneous by thin layer chromatography. It was characterized as the oxalate salt, melting point 167°-169° (dec.).

Workup

  1. temperaturethe mixture was heated at 80°C
  2. custom(1 hour)
  3. customvolatiles were removed in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with chloroform
  6. dry with materialAfter drying with sodium sulfate

Sources & evidence

ORD record
ord-34b7ffc63849428aad38757b47af9fac
Source dataset
uspto-grants-1976_03
Patent number
US03947445

Reaction notes

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