Pyridine → 2,3-Dicyano-5-chloro-6-ethylthiopyrazine

HRID 128400Notes

Reaction equation

HRID 128400 reaction equation
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6](Cl)=[C:5]([Cl:12])[N:4]=1)#[N:2].[CH2:13]([SH:15])[CH3:14].N1C=CC=CC=1>CC(C)=O.O>[C:9]([C:8]1[C:3]([C:1]#[N:2])=[N:4][C:5]([Cl:12])=[C:6]([S:15][CH2:13][CH3:14])[N:7]=1)#[N:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6343EthanethiolHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

Product 1

HCID 128737542,3-Dicyano-5-chloro-6-ethylthiopyrazineYield 29.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2,3-Dicyano-5,6-dichloropyrazine (1.00 g; 0.005 mole) and 0.47 g of ethanethiol were dissolved in 50 ml of acetone. The solution was cooled to -15° to -10° C., and a solution of 0.40 g (0.005 mole) of pyridine in 40 ml of water was added dropwise over the period of 30 minutes. The mixture was worked up in the same way as in Example 26 to afford 0.33 g (yield 29%) of 2,3-dicyano-5-chloro-6-ethylthiopyrazine.

Workup

  1. temperatureThe solution was cooled to -15° to -10° C.

Sources & evidence

ORD record
ord-2fa57c2e3a6e4c388415e2d2b4985a1a
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Reaction notes

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