Formic Acid → HCID 10442279, compound

HRID 1607575Notes

Reaction equation

HRID 1607575 reaction equation
Br.[CH3:2][N:3]1[N:7]=[N:6][C:5]([C:8]2[CH2:9][NH:10][CH2:11][CH2:12][CH:13]=2)=[N:4]1.[CH:14](O)=O>C=O>[CH3:2][N:3]1[N:7]=[N:6][C:5]([C:8]2[CH2:9][N:10]([CH3:14])[CH2:11][CH2:12][CH:13]=2)=[N:4]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 131716105HCID 131716105, compound

Product 1

HCID 10442279HCID 10442279, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 8 (0.70 g, 0.0028 mol) in formic acid (20 ml) and 35% formaldehyde (7 ml) was refluxed overnight. The solution was evaporated in vacuo, and the residue was taken up in ether (20 ml) and 28% sodium hydroxide (20 ml). The phases were separated, and the aqueous phase was extracted three times with dichloromethane (20 ml). The combined organic phases were washed four times with saturated sodium chdloride solution (20 ml). The organic phase was dried over magnesium sulphate and evaporated in vacuo yielding 0.60 g or crude 10. Crystallization from ether-light petroleum gave 0.37 g (0.0021 mol, 74%) of title compound, M.P. 86°-87° C. Anal. (C8H13N5) C, H, N.

Workup

  1. customThe solution was evaporated in vacuo
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three times with dichloromethane (20 ml)
  4. washThe combined organic phases were washed four times with saturated sodium chdloride solution (20 ml)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customevaporated in vacuo
  7. customyielding 0.60 g or crude 10
  8. customCrystallization from ether-light petroleum

Sources & evidence

ORD record
ord-b2b69b5b0012474c8732612f172f3d1b
Source dataset
uspto-grants-1989_09
Patent number
US04866077

Reaction notes

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