Triethylamine → HCID 19898936, compound

HRID 1607120Notes

Reaction equation

HRID 1607120 reaction equation
[CH2:1]([N:8]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][O:20]2)=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][NH:23][CH2:24][CH2:25][N:26]1[N:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36].C(N(CC)CC)C>C(O)(C)C>[CH2:1]([N:8]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]([OH:20])[CH2:21][N:23]([CH2:24][CH2:25][N:26]2[N:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH3:22])=[CH:17][CH:18]=1)[S:9]([CH3:12])(=[O:10])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 198989582-[2-(Methylamino)ethyl]phthalazin-1(2H)-oneHCID 54231897HCID 54231897, compound

Product 1

HCID 19898936HCID 19898936, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-[4-(N-Benzylmethanesulphonamido)phenyl]oxirane (1.5 g), N-methyl-2-(phthalazin-1-on-2-yl)ethylamine (1.4 g) and triethylamine (1.4 g) in isopropanol (50 ml) were stirred at reflux temperature for 5 hours. The solvent was evaporated, the residue dissolved in methylene chloride and washed three times with sodium carbonate solution and three times with brine. The organic layer was dried and evaporated to give an oil which was purified by column chromatography on silica, "Kieselgel 60" (Merck, Trade Mark), eluting with methylene chloride containing methanol (0% up to 2%). Combination and evaporation of the appropriate fractions gave a foam which was chromatographed a second time on silica, "Kieselgel 60" (Merck, Trade Mark), eluting with methyl isobutyl ketone (MIBK) containing acetone (0% up to 20%). The appropriate fractions were combined and evaporated then re-evaporated from diethyl ether to give the title compound as a foam, yield 450 mg.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in methylene chloride
  4. washwashed three times with sodium carbonate solution and three times with brine
  5. customThe organic layer was dried
  6. customevaporated
  7. customto give an oil which
  8. customwas purified by column chromatography on silica, "Kieselgel 60" (Merck, Trade Mark)
  9. washeluting with methylene chloride
  10. additioncontaining methanol (0% up to 2%)
  11. customCombination and evaporation of the appropriate fractions
  12. customgave a foam which
  13. customwas chromatographed a second time on silica, "Kieselgel 60" (Merck, Trade Mark)
  14. washeluting with methyl isobutyl ketone (MIBK)
  15. additioncontaining acetone (0% up to 20%)
  16. customevaporated
  17. customthen re-evaporated from diethyl ether

Sources & evidence

ORD record
ord-cc9efdeba7c34027ba41d903c971571a
Source dataset
uspto-grants-1989_09
Patent number
US04863948

Reaction notes

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