Hydrochloric Acid → HCID 462094, compound

HRID 1862396Notes

Reaction equation

HRID 1862396 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:23])[C:5]2[C:10]([CH2:11][NH:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)=[CH:9][O:8][C:6]=2[N:7]=1.[CH2:24]=O.[C-]#N.[Na+].Cl>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([NH2:23])[C:5]2[C:10]([CH2:11][N:12]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=3)[CH3:24])=[CH:9][O:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8929Sodium CyanideHCID 457719HCID 457719, compound

Product 1

HCID 462094HCID 462094, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of compound 424 (0.10 g, 0.32 mmol), 30% (w/w) aqueous solution of formaldehyde (0.1 ml) and NaCN BH3 (0.063 g) in acetonitrile (10 ml) was added dropwise concentrated hydrochloric acid until the suspension dissolved. The solution was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the residue dissolved in a minimum amount of distilled water and the pH of the solution adjusted to 7 with concentrated NH4OH. The resulting suspension was sonicated, cooled to 5° C. and filtered. The residue was washed with cold water (2×3 ml), stirred in MeOH (5 ml) for 12 h and filtered. The residue was washed with MeOH (2×3 ml) to afford 0.065 g (64%) of compound 429 as a light yellow solid.

Workup

  1. dissolutiondissolved
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in a minimum amount of distilled water
  4. customThe resulting suspension was sonicated
  5. temperaturecooled to 5° C.
  6. filtrationfiltered
  7. washThe residue was washed with cold water (2×3 ml)
  8. stirringstirred in MeOH (5 ml) for 12 h
  9. filtrationfiltered
  10. washThe residue was washed with MeOH (2×3 ml)

Sources & evidence

ORD record
ord-d71f915a6de24a97891fdcb08a338c3c
Source dataset
uspto-grants-2003_03
Patent number
US06537999B2

Reaction notes

Loading…