Triethylamine → 3-((2-Benzothiazolylmethyl)amino)-5-ethyl-6-methylpyridin-2(1H)-one

HRID 1032990Notes

Reaction equation

HRID 1032990 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[NH:4][C:5]([CH3:10])=[C:6]([CH2:8][CH3:9])[CH:7]=1.Cl[CH2:13][C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.C(N(CC)CC)C>C(O)C>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[CH2:13][NH:1][C:2]1[C:3](=[O:11])[NH:4][C:5]([CH3:10])=[C:6]([CH2:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3049782-(Chloromethyl)benzothiazoleHCID 4810223-Amino-5-ethyl-6-methyl-1H-pyridin-2-one

Product 1

HCID 4534373-((2-Benzothiazolylmethyl)amino)-5-ethyl-6-methylpyridin-2(1H)-oneYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-amino-5-ethyl-6-methyl-2-(1H)-pyridinone (152 mg, 1.0 mmol), 2-chloromethyl-1,3-benzthiazole (184 mg, 1.0 mmol) and triethylamine (0.14 mL, 1.0 mmol) in absolute ethanol (5 mL) was stirred at reflux for 24 hours. After filtering and concentrating under reduced pressure, the residue was flash chromatographed over silica gel. Elution with 4% MeOH- 96% CHCl3 gave 233 mg of product. Recrystallization from EtOH-water gave 77 mg of analytically pure product, mp 209°-210° C. Anal. Calcd for C16H17N3OS: C, 67.83; H, 6.05; N, 14.83. Found: C, 67.71; H, 6.03; N, 14.70.

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationAfter filtering
  3. concentrationconcentrating under reduced pressure
  4. customchromatographed over silica gel
  5. washElution with 4% MeOH- 96% CHCl3

Sources & evidence

ORD record
ord-5c69f4c288ff4e7192f934945f456c0b
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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