Oxalyl chloride → 2-Methylsulfanyl-pyrimidine-4-carbonyl chloride

HRID 2415692Notes

Reaction equation

HRID 2415692 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][N:4]=1.C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]([Cl:15])=[O:11])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2957752-(Methylsulfanyl)pyrimidine-4-carboxylic acid

Product 1

HCID 115429012-Methylsulfanyl-pyrimidine-4-carbonyl chlorideYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylsulfanyl-pyrimidine-4-carboxylic acid (20 g, 117.7 mmol) in CH2Cl2 (100 mL) is added oxalyl chloride (17.2 g, 197 mmol) and DMF (20 drops). The reaction solution is stirred at room temperature for 18 hours after which the solvent is removed in vacuo to afford 21.2 g, (95% yield) of the desired product as a dark green solid.

Workup

  1. customis removed in vacuo

Sources & evidence

ORD record
ord-c25c2e660a564fbe91d9203fcae3d808
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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