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

HRID 1462305Notes

Reaction equation

HRID 1462305 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-e45b35f256e542e4923d2ef801e67df9
Source dataset
uspto-grants-1984_07
Patent number
US04460403

Reaction notes

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