HCID 9998883, compound → HCID 3000382, compound

HRID 1033003Notes

Reaction equation

HRID 1033003 reaction equation
C([S:5][C:6]1[C:11]([NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[CH:10][C:9]([CH2:24][CH3:25])=[C:8]([CH3:26])[N:7]=1)(C)(C)C.Cl.N1C=CC=CC=1>O>[CH2:24]([C:9]1[CH:10]=[C:11]([NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[C:6](=[S:5])[NH:7][C:8]=1[CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 9998883HCID 9998883, compoundHCID 10176127Pyridinium chloride

Product 1

HCID 3000382HCID 3000382, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-tert-butylthio-5-ethyl-6-methyl-3-(2-napthylmethylamino)pyridine (98 mg, 0.27 mmol) and pyridine hydrochloride (0.45 g, 3.8 mmol) was heated under an atmosphere of nitrogen at 140° C. until evolution of gas ceased (about 45 minutes). Water was added and the resultant mixture was extracted three times with chloroform. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure (15 torr). The residue was then subjected to column chromatography on silica gel (eluted with 2% methanol in ethyl acetate). Collection and concentration of appropriate fraction yielded 32 mg (36%) of the pyridinethione. Anal. Calcd for C19H20N2S·0.25 EtOAc: C, 72.68; H, 6.71; N, 8.48. Found: C, 72.41; H, 6.59; N, 8.86.

Workup

  1. custom(about 45 minutes)
  2. extractionthe resultant mixture was extracted three times with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure (15 torr)
  6. customCollection and concentration of appropriate fraction

Sources & evidence

ORD record
ord-e4a453e226234196a081e3b9b0928b78
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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