Acetonitrile → HCID 21690601, compound

HRID 1033030Notes

Reaction equation

HRID 1033030 reaction equation
N[C:2]1[C:3](=[O:11])[NH:4][C:5]([CH3:10])=[C:6]([S:8][CH3:9])[CH:7]=1.Cl[CH2:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.C([N:26](C(C)C)CC)(C)C.C(#N)C>C(Cl)Cl.CC(O)C.C(Cl)Cl>[O:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[CH2:13][C:2]1[C:3](=[O:11])[N:4]([NH2:26])[C:5]([CH3:10])=[C:6]([S:8][CH3:9])[CH:7]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 20619892-(Chloromethyl)-1,3-benzoxazoleHCID 10012332HCID 10012332, compound

Product 1

HCID 21690601HCID 21690601, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21966342Isopropanol methylene chlorideSolvent3×

Procedure

A mixture of 3-amino-5-methylthio-6-methylpyridin-2(1H)-one (0.201 g, 0.0013 mol), 2-chloromethylbenzoxazole (0.239 g, 0.0014 mol), diisopropylethylamine (0.181 g, 0.0014 mol), and acetonitrile (6 mL) was heated at reflux under nitrogen for 35 hours. The dark solids which had formed were removed by filtration (0.089 g), and the filtrate evaporated to dryness. The two fractions were combined and chromatographed on a 30 mm column containing 230-400 mesh silica gel (6 inches). The column was prepared with methylene chloride and the crude product applied in methylene chloride. Development of the column was with 2% 2-propanol/methylene chloride (500 mL), 5% 2-propanol/methylene chloride (500 mL), and 10% 2-propanol/methylene chloride (1000 mL). Concentration of the fractions containing the desired product gave 0.133 g (33.5% yield) of 3-[(2-Benzoxazolyl)methyl]amino-5-methylthio-6-methylpyridin-2(1H)-one m.p. 180°-181° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 35 hours
  3. customThe dark solids which had formed
  4. customwere removed by filtration (0.089 g)
  5. customthe filtrate evaporated to dryness
  6. customchromatographed on a 30 mm column
  7. additioncontaining 230-400 mesh silica gel (6 inches)
  8. customThe column was prepared with methylene chloride

Sources & evidence

ORD record
ord-6b1b3b2a74d64dd790049426623a0d70
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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