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

HRID 2096860Notes

Reaction equation

HRID 2096860 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 abtained 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-ae16a04c160e4a83a0a41ee08d543e4d
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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