Oxalyl chloride → 3-Methyl-2-oxo-1,3-benzoxazole-5-carbonyl chloride

HRID 2386853Notes

Reaction equation

HRID 2386853 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11](O)=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:14].C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]([Cl:18])=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:14]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 99901743-Methyl-2-oxo-2,3-dihydro-1,3-benzoxazole-5-carboxylic acid

Product 1

HCID 104431423-Methyl-2-oxo-1,3-benzoxazole-5-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-methyl-2-oxo-2,3-dihydro-benzooxazole-5-carboxylic acid (2.50 g, obtained in Example 116, step 5) in CH2Cl2 (40 mL) were added nine drops of DMF and oxalylchloride (1.78 mL). The mixture was stirred at room temperature for 2 hours and was then concentrated to dryness. The resulting solid was dried at high vacuum over night. The title compound was obtained as a colorless solid (2.85 g, 99%). MS (EI)=211.0 [M+].

Workup

  1. concentrationwas then concentrated to dryness
  2. customThe resulting solid was dried at high vacuum over night

Sources & evidence

ORD record
ord-bde5d916daf54408b989e7d411f09849
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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