Pyridine → 5-Chloro-6-[(3-methylphenyl)sulfanyl]pyrazine-2,3-dicarbonitrile

HRID 1763817Notes

Reaction equation

HRID 1763817 reaction equation
N1C=CC=CC=1.Cl[C:8]1[C:13]([Cl:14])=[N:12][C:11]([C:15]#[N:16])=[C:10]([C:17]#[N:18])[N:9]=1.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([SH:26])[CH:21]=1>ClCCCl>[Cl:14][C:13]1[N:12]=[C:11]([C:15]#[N:16])[C:10]([C:17]#[N:18])=[N:9][C:8]=1[S:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 79303-ThiocresolHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

Product 1

HCID 128737685-Chloro-6-[(3-methylphenyl)sulfanyl]pyrazine-2,3-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Pyridine (2.37 g) was mixed rapidly with a solution of 6.00 g of 2,3-dichloro-5,6-dicyanopyrazine in 240 ml of 1,2-dichloroethane. After 15 minutes the well stirred mixture, protected from moisture, was cooled to -30° and 3.72 g of m-thiocresol was added in one portion. The temperature was maintained at -30° for 0.5 hour and then was allowed to return to ambient over the course of 2 hours. The mixture was then washed with water to remove pyridine hydrochloride, dried over MgSO4, and concentrated on a rotary evaporator to a solid residue. The residue was purified by the technique of dry column chromatography using silica gel adsorbent and 1-chlorobutane as solvent and eluent. The yield of pure product was 6.9 g, mp 117°-119°.

Workup

  1. temperaturewas cooled to -30°
  2. temperatureThe temperature was maintained at -30° for 0.5 hour
  3. customto ambient over the course of 2 hours
  4. washThe mixture was then washed with water
  5. customto remove pyridine hydrochloride
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated on a rotary evaporator to a solid residue
  8. customThe residue was purified by the technique of dry column chromatography

Sources & evidence

ORD record
ord-d0486e43977a46a292f6dd5195983761
Source dataset
uspto-grants-1978_09
Patent number
US04113724

Reaction notes

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