Nitrogen → 2-Methyl-5-m-tolyl-oxazole-4-carbonyl chloride

HRID 1189377Notes

Reaction equation

HRID 1189377 reaction equation
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[C:7]([C:9](O)=[O:10])[N:8]=1.CN(C=O)C.C(Cl)(=O)C([Cl:27])=O>C1(C)C=CC=CC=1>[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[C:7]([C:9]([Cl:27])=[O:10])[N:8]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acid

Product 1

HCID 866649052-Methyl-5-m-tolyl-oxazole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 2-methyl-5-m-tolyl-oxazole-4-carboxylic acid (53 mg, 0.25 mmol) in toluene (1.0 mL) was treated with a drop of DMF followed by oxalyl chloride (0.08 mL, 0.86 mmol) and the resulting yellow solution was stirred at rt for 30 min. The solvent was then removed under reduced pressure (coevaporation with toluene) to give 2-methyl-5-m-tolyl-oxazole-4-carbonyl chloride.

Workup

  1. customThe solvent was then removed under reduced pressure (coevaporation with toluene)

Sources & evidence

ORD record
ord-0c90cb6dbb304fe6a2eaee3197e9239f
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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