Nitrogen → 5-Phenyl-1,3-oxazole-4-carbonyl chloride

HRID 1189375Notes

Reaction equation

HRID 1189375 reaction equation
N#N.[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([OH:16])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C=O)C.C(Cl)(=O)C([Cl:25])=O>C1(C)C=CC=CC=1>[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([Cl:25])=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acid

Product 1

HCID 27763005-Phenyl-1,3-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 commercially available 5-phenyl-oxazole-4-carboxylic acid (67 mg, 0.35 mmol) in toluene (1.0 mL) was treated with a drop of DMF followed by oxalyl chloride (0.08 mL, 0.91 mmol) and the resulting yellow solution was stirred at rt for 1 h. The solvent was then removed under reduced pressure (co-evaporation with toluene) to give 5-phenyl-oxazole-4-carbonyl chloride as a brown oil.

Workup

  1. customThe solvent was then removed under reduced pressure (co-evaporation with toluene)

Sources & evidence

ORD record
ord-11605672062f406c929751ac86c97342
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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