Pyridinium chloride → HCID 19086253, compound

HRID 1033014Notes

Reaction equation

HRID 1033014 reaction equation
C([S:5][C:6]1[C:11]([CH2:12][NH:13][C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][C:9]([CH2:23][CH3:24])=[C:8]([CH3:25])[N:7]=1)(C)(C)C.Cl.N1C=CC=CC=1>O>[O:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[NH:13][CH2:12][C:11]1[C:6](=[S:5])[NH:7][C:8]([CH3:25])=[C:9]([CH2:23][CH3:24])[CH:10]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 19086262HCID 19086262, compound

Product 1

HCID 19086253HCID 19086253, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-t-butylthio-3-{[(benzoxazol-2-yl)amino]methyl}-5-ethyl-6-methylpyridine (78 mg, 0.22 mmol) and pyridine hydrochloride (325 mg, 2.81 mmol) was warmed in a pre-heated oil bath at 150° C. for 25 minutes. The mixture was cooled, diluted with water and the yellow precipitated product was collected by filtration. This residue was dissolved in methylene chloride, filtered through a pad of charcoal and then hexane was added and the methylene chloride boiled off as the product crystallized out to yield 42 mg (64%), m.p. 238°-240° C. Anal Calcd. for C16H17N3OS: C, 64.18; H, 5.72; N, 14.04. Found: C, 63.86; H, 5.69; N, 13.81.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe yellow precipitated product was collected by filtration
  3. dissolutionThis residue was dissolved in methylene chloride
  4. filtrationfiltered through a pad of charcoal
  5. additionhexane was added
  6. customcrystallized out
  7. customto yield 42 mg (64%), m.p. 238°-240° C

Sources & evidence

ORD record
ord-c804be28f62d4d3998ac1f9c972415ba
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

Loading…