Hydrochloric Acid → HCID 14519825, compound

HRID 1084781Notes

Reaction equation

HRID 1084781 reaction equation
[C:1]([N:5]([CH2:7][CH2:8][OH:9])[NH2:6])([CH3:4])([CH3:3])[CH3:2].[ClH:10].[C-:11]#[N:12].[K+].[CH2:14]=O.[N:16]([O-:18])=O.[Na+]>O.C(O)C>[ClH:10].[C:1]([N:5]([CH2:7][CH2:8][OH:9])[N+:6]1[N-:16][O:18][C:11](=[NH:12])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 9032Potassium CyanideHCID 14519823HCID 14519823, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14519825HCID 14519825, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

The oil obtained in stage c (14 g) is dissolved in 50 ml of water and 8.1 g of concentrated hydrochloric acid and the solution is cooled to -5° C. A solution of 6.6 g of potassium cyanide in 20 ml of water is then added dropwise. After addition of 15 ml of ethanol, a 39% strength formalin solution (8.2 g) is added dropwise and the pH of the mixture is brought to 7. The mixture is stirred at room temperature for 2 hours and brought to pH 1.5 with concentrated hydrochloric acid, and a solution of 5.6 g of sodium nitrite in 25 ml of water is added dropwise, while cooling with ice. The mixture is subsequently stirred at room temperature overnight and then extracted with diethyl ether, and the extract is dried and concentrated. The oil which remains is dissolved in 50 ml of concentrated methanolic hydrochloric acid and the solution is diluted with 50 ml of ethyl acetate. The precipitate which has separated out is filtered off with suction and discarded. After 2 hours, the filtrate is concentrated, the residue is stirred with ethyl acetate and the solid is filtered off with suction and recrystallized from ethanol/diethyl ether (1:2). Yield: 5.9 g melting point=161°-163° C. (decomp.)

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture is subsequently stirred at room temperature overnight
  3. extractionextracted with diethyl ether
  4. customthe extract is dried
  5. concentrationconcentrated
  6. dissolutionThe oil which remains is dissolved in 50 ml of concentrated methanolic hydrochloric acid
  7. additionthe solution is diluted with 50 ml of ethyl acetate
  8. customThe precipitate which has separated out
  9. filtrationis filtered off with suction
  10. waitAfter 2 hours
  11. concentrationthe filtrate is concentrated
  12. stirringthe residue is stirred with ethyl acetate
  13. filtrationthe solid is filtered off with suction
  14. customrecrystallized from ethanol/diethyl ether (1:2)

Sources & evidence

ORD record
ord-9ab8e80386094e89b9fec5ef4042df6e
Source dataset
uspto-grants-1991_04
Patent number
US05006540

Reaction notes

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