110714-14-2 → HCID 14551079, compound

HRID 1761398Notes

Reaction equation

HRID 1761398 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9](=[O:12])[NH:10][N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[ClH:13].[Cl:14][CH2:15][CH2:16][N:17]([CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Na].C(O)C>[ClH:14].[ClH:13].[CH2:18]([N:17]([CH2:16][CH2:15][N:10]1[C:9](=[O:12])[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[N:11]1)[CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 14551076110714-14-2HCID 14551077N-Benzyl-2-chloro-N-(2-phenoxyethyl)ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 14551079HCID 14551079, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 5360545SodiumSolvent2×

Procedure

2.43 g (0.015 mole) of 6-(1-imidazolyl)-3(2H)-pyridazinone are dissolved in the solution of 0.35 g (0.015 g-atom) of sodium in 12 ml of absolute ethanol and the solution is stirred at room temperature for 15 minutes. To the thus-obtained suspension, the base liberated from the solution of 4.89 g (0.015 mole) of N-(2-chloroethyl)-N-(2-phenoxyethyl)-N-benzylamine hydrochloride [dissolved in 12 ml of absolute ethanol by adding a solution of 0.35 g (0.015 g-atom) of sodium in 12 ml of absolute ethanol] is added, thereupon the mixture is stirred at room temperature for 30 minutes and then boiled under reflux while stirring for 4 hours, set aside overnight at room temperature and evaporated. The residue is taken up in 200 ml of chloroform, filtered, the organic solution is washed with water, dried and evaporated under reduced pressure. The residue weighing 5.82 g is dissolved in absolute acetone and a calculated amount of ethanolic hydrogen chloride solution is added, diluted with isopropanol and kept in the refrigerator overnight. The precipitate is filtered off, washed with acetone and dried to give 5.9 g (80% yield) of the aimed product, m. p. 153°-156° C.

Workup

  1. additionis added
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. temperatureunder reflux
  4. stirringwhile stirring for 4 hours
  5. waitset aside overnight at room temperature
  6. customevaporated
  7. filtrationfiltered
  8. washthe organic solution is washed with water
  9. customdried
  10. customevaporated under reduced pressure
  11. dissolutionis dissolved in absolute acetone
  12. additiona calculated amount of ethanolic hydrogen chloride solution is added
  13. additiondiluted with isopropanol
  14. customkept in the refrigerator overnight
  15. filtrationThe precipitate is filtered off
  16. washwashed with acetone
  17. customdried

Sources & evidence

ORD record
ord-612512b0cb114b33bad4c8b9189f900d
Source dataset
uspto-grants-1989_05
Patent number
US04826845

Reaction notes

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