Oxalyl chloride → 2-Chloro-4-methylpyrimidine-5-carbonyl chloride

HRID 1584840

Reaction equation

HRID 1584840 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([OH:11])=O)=[CH:4][N:3]=1.C(Cl)(=O)C([Cl:15])=O>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([Cl:15])=[O:11])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 104874142-Chloro-4-methylpyrimidine-5-carboxylic acid

Product 1

HCID 212206502-Chloro-4-methylpyrimidine-5-carbonyl chlorideYield 61.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-4-methylpyrimidine-5-carboxylic acid (0.81 g, 4.70 mmol), oxalyl chloride (0.89 g, 7.05 mmol), DMF (2 drops) in CH2Cl2 (23 mL) was stirred at room temperature under N2 for 4 h. The solution was concentrated and distilled to give the title compound (0.55 g, 61%); b.p. 90-100° C., 1.3 mm/Hg; 1H NMR (CDCl3) δ d9.02 (s, 1H), 2.74 (s, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. distillationdistilled

Sources & evidence

ORD record
ord-d375475290144e0fa6610171f81d8166
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Linked notes

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