Pyridine → 5-Isothiocyanatopyrazine-2-carbonitrile

HRID 1878306Notes

Reaction equation

HRID 1878306 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[N:7]=[CH:8][C:9]([C:12]#[N:13])=[N:10][CH:11]=1.N1C=CC=CC=1>C1COCC1.C(Cl)Cl>[N:5]([C:6]1[N:7]=[CH:8][C:9]([C:12]#[N:13])=[N:10][CH:11]=1)=[C:1]=[S:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10040ThiophosgeneHCID 139252945-Aminopyrazine-2-carbonitrile

Product 1

HCID 583058265-Isothiocyanatopyrazine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of thiophosgene (1.86 g, 15 mmol) in THF (4 mL) is added dropwise to a solution of 5-aminopyrazine-2-carbonitrile (1.20 g, 10 mmol) and pyridine (2 mL) in CH2Cl2 (200 mL) and THF (25 mL) at room temperature. The reaction mixture is stirred at room temperature for 3 h. The mixture is concentrated and the crude product is diluted with ethyl acetate, filtered and concentrated to give the title compound.

Workup

  1. concentrationThe mixture is concentrated
  2. additionthe crude product is diluted with ethyl acetate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e1aadf4717934866bb9566d76da8d861
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

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