Hydrochloric Acid → HCID 178524750, compound

HRID 1525204Notes

Reaction equation

HRID 1525204 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH2:10])=[NH:9].C[O-].[Na+].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21]CC)=[O:20])C.[OH-].[K+].Cl>CO.O>[OH:16][C:17]1[C:18]([C:19]([OH:21])=[O:20])=[CH:24][N:10]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[N:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 12403615Pyridine-2-carboximidamide hydrochloride

Product 1

HCID 178524750HCID 178524750, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To picolinamidine hydrochloride (1-1-g) (112 g, 0.71 mol) in MeOH (1.1 L) was added sodium methoxide (39.4 g, 0.71 mol) and diethyl ethoxymethylenemalonate (142 g, 0.71 mol). The reaction mixture was heated at reflux overnight and then cooled to room temperature. The resulting mixture was filtered and to the filtrate was added potassium hydroxide (71.4 g, 1.37 mol) in water (265 mL). The reaction was heated at reflux for 2 h. The reaction was cooled to room temperature before adding concentrated HCl (180 mL, 2.35 mol) in portions. The reaction was aged for 2 h. The solids were filtered and rinsed with EtOH, Et2O and then hexane to provide the product, 1-1-h, (110 g, 65%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe resulting mixture was filtered and to the filtrate
  4. temperatureThe reaction was heated
  5. temperatureat reflux for 2 h
  6. temperatureThe reaction was cooled to room temperature
  7. filtrationThe solids were filtered
  8. washrinsed with EtOH, Et2O
  9. customhexane to provide the product, 1-1-h, (110 g, 65%)

Sources & evidence

ORD record
ord-b143c037c7da4ef290652661be4b7a01
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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