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

HRID 1189370Notes

Reaction equation

HRID 1189370 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 (74 mg, 0.34 mmol) in toluene (2.0 mL) was treated with a drop of DMF followed by oxalyl chloride (0.10 mL, 1.18 mmol) and the resulting yellow solution was stirred at rt for 1 h. 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-b7f5be39afb64797b78f4c924df38f32
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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