Ethanol → 2-Hydroxy-2-(4-methanesulphonamidophenyl)-N-methyl-N-[2-(5-phenyl-2H-pyridazin-3-on-2-yl)ethyl] ethylamine

HRID 1607113Notes

Reaction equation

HRID 1607113 reaction equation
[C:1]1([C:7]2[C:8](=O)[N:9](CCBr)[N:10]=[CH:11]C=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:17][CH:18]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=1)[CH2:19][NH:20][CH3:21].[CH2:33](N(CC)CC)C.[CH2:40]([OH:42])[CH3:41]>>[OH:17][CH:18]([C:22]1[CH:23]=[CH:24][C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:26][CH:27]=1)[CH2:19][N:20]([CH3:33])[CH2:21][CH2:11][N:10]1[C:40](=[O:42])[CH:41]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 119542852-Hydroxy-N-methyl-2-(4-methanesulphonamidophenyl)ethylamineHCID 198529152-[-Phenyl-2H-pyridazin-3-on-2-yl]ethyl bromide

Product 1

HCID 198989472-Hydroxy-2-(4-methanesulphonamidophenyl)-N-methyl-N-[2-(5-phenyl-2H-pyridazin-3-on-2-yl)ethyl] ethylamine

Procedure

2-[-Phenyl-2H-pyridazin-3-on-2-yl]ethyl bromide (0.28 g), 2-hydroxy-N-methyl-2-(4-methanesulphonamidophenyl)ethylamine (0.24 g) and triethylamine (0.22 g) were refluxed in ethanol (30 ml) for 4 hours. The solvent was removed and the residue taken up in methylene chloride, washed with water, evaporated and the residue chromatographed on silica [Merck `Kieselgel 60` (Trade Mark)], eluting with ethyl acetate. Collection and evaporation of appropriate fractions gave the title compound as a solid which was recrystallised from diisopropyl ether, yield 0.1 g, m.p. 108°.

Workup

  1. customThe solvent was removed
  2. washwashed with water
  3. customevaporated
  4. customthe residue chromatographed on silica [Merck `Kieselgel 60` (Trade Mark)],
  5. washeluting with ethyl acetate
  6. customCollection and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-ca2f7bb6f19c40aa876b9ad27b488f84
Source dataset
uspto-grants-1989_09
Patent number
US04863948

Reaction notes

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