Formic Acid → HCID 22325080, compound

HRID 496074Notes

Reaction equation

HRID 496074 reaction equation
[ClH:1].[CH3:2][NH:3][C:4]1([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5]1.[CH:15](O)=O.C=O.[OH-].[Na+]>O>[ClH:1].[CH3:2][N:3]([CH3:15])[C:4]1([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 22325164HCID 22325164, compound

Product 1

HCID 22325080HCID 22325080, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

1.07 g of the compound of Example 18 diluted with 1.2 ml of water are added to a solution, cooled to 0° C., of 1.38 g of formic acid, 1.12 ml of 37% formaldehyde in water and 0.15 ml of distilled water. The reaction mixture is heated at reflux for 16 hours and is then cooled to 0° C. and 10 ml of 4N sodium hydroxide solution are added. The mixture is extracted with ether. The organic phase is treated in customary manner and evaporated. The residue is taken up in ethanol, concentrated again and then diluted with 20 ml of ether and 4 ml of 4N hydrochloric acid solution in dioxane. The mixture is stirred for 20 minutes, filtered, rinsed with ether and dried, allowing the expected product to be isolated.

Workup

  1. additionare added to a solution
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 16 hours
  4. extractionThe mixture is extracted with ether
  5. additionThe organic phase is treated in customary manner
  6. customevaporated
  7. concentrationconcentrated again
  8. additiondiluted with 20 ml of ether and 4 ml of 4N hydrochloric acid solution in dioxane
  9. filtrationfiltered
  10. washrinsed with ether
  11. customdried
  12. customto be isolated

Sources & evidence

ORD record
ord-5cf82cae9a0c402f943b86f26cfc24ce
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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