Pyridine → HCID 14304054, compound

HRID 2350972Notes

Reaction equation

HRID 2350972 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][C:17](=O)[C:16]([CH3:27])=[C:15]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:35]>O>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][C:17](=[S:35])[C:16]([CH3:27])=[C:15]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 14303549HCID 14303549, compound

Product 1

HCID 14304054HCID 14304054, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 40 ml of pyridine were added 1.3 g (0.0035 mole) of 1-(2-chlorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone and 0.9 g (0.0042 mole) of phosphorus pentasulfide, followed by refluxing the resultant mixture for 3 hours. After cooling, the reaction mixture was poured into water and the resulting crystals were collected by filtration. The crystals were dissolved in 100 ml of chloroform, and washed first with 30 ml of 2N hydrochloric acid and then with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate. After washing the chloroform solution further with water, it was dried over anhydrous sodium sulfate. After removal of sodium sulfate, the solvent was distilled off to obtain crystals. The crystals were recrystallized from a 1:1 mixture of acetone and hexane, thereby obtaining 1.1 g of 1-(2-chlorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinethione having a melting point of 271°-275° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting crystals were collected by filtration
  3. dissolutionThe crystals were dissolved in 100 ml of chloroform
  4. washwashed first with 30 ml of 2N hydrochloric acid
  5. washAfter washing the chloroform solution further with water, it
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customAfter removal of sodium sulfate
  8. distillationthe solvent was distilled off
  9. customto obtain crystals
  10. customThe crystals were recrystallized from a 1:1 mixture of acetone and hexane

Sources & evidence

ORD record
ord-da0556e31421423697ebb7e23a69bc45
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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