HCID 19742755, compound → HCID 57186192, compound

HRID 2254556Notes

Reaction equation

HRID 2254556 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH3:18])[CH:9]=2)=[CH:6][CH:7]=1.[N:19]#[C:20][NH2:21].[Na]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN1CCCC1=O.S(=O)(=O)(O)O>[C:20]([NH:21][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH3:18])[CH:9]=2)=[CH:6][CH:7]=1)#[N:19]

Participants

6

Reactant 2

HCID 19742755HCID 19742755, compoundHCID 57375518Cyanamidnatrium

Product 1

HCID 57186192HCID 57186192, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1118Sulfuric AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2.7 g 3-chloro-6-(3-ethoxy-4-methoxyphenyl)pyridazine, 1.3 g sodium cyanamide and 0.5 g benzyltriethylammonium chloride are heated at 150° C. in 30 ml N-methylpyrrolidone for 3 hours. After cooling the reaction solution is diluted with 200 ml 1N sulphuric acid and extracted 3 times with 50 ml chloroform each time. The combined extracts are dried over sodium sulphate and evaporated and the residue is boiled up in isopropanol. The crystalline product is filtered off with suction, washed with isopropanol and dried in vacuo. This gives 2.6 g (96.3%) of the title compound of m.p. 206° C.

Workup

  1. temperatureAfter cooling the reaction solution
  2. extractionextracted 3 times with 50 ml chloroform each time
  3. dry with materialThe combined extracts are dried over sodium sulphate
  4. customevaporated
  5. filtrationThe crystalline product is filtered off with suction
  6. washwashed with isopropanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-cde8a7c854e5416b9c7aaf67d3b99239
Source dataset
uspto-grants-1993_08
Patent number
US05236918

Reaction notes

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