Dimethylformamide → 5-Chloropyrazine-2-carbonyl chloride

HRID 1027696Notes

Reaction equation

HRID 1027696 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C)C=O.C(Cl)(C([Cl:20])=O)=O>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([Cl:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 4654725-Chloropyrazinoic acid

Product 1

HCID 152157435-Chloropyrazine-2-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-chloropyrazine-2-carboxylic acid (1.00 gram, 6.31 mmol) in dichloromethane (30 ml) was treated with catalytic amount of dimethylformamide, followed by (COCl)2 (0.85 ml, 9.46 mmol). The resulting mixture was stirred over night. The reaction was concentrated in vacuo, and dried under vacuum to give desired 5-chloropyrazine-2-carbonyl chloride as solid (1.05 g, 100%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customdried under vacuum

Sources & evidence

ORD record
ord-7f4b089fdf43449ea6411350b8e80328
Source dataset
uspto-grants-2014_05
Patent number
US08735396B2

Reaction notes

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