2-Methylbenzoxazole → HCID 14972993, compound

HRID 868917

Reaction equation

HRID 868917 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C[C:12]([N:14]([CH3:16])[CH3:15])=O>CN(C=O)C>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1/[CH:1]=[CH:12]/[N:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 72252-MethylbenzoxazoleHCID 31374Dimethylacetamide

Product 1

HCID 14972993HCID 14972993, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 2-methylbenzo[d]oxazole (3 g, 22.6 mmol) in DMF (3.2 g) and dimethyl acetamide (3.5 g, 29.3 mmol) was stirred under N2 at 145° C. overnight. Then the solution was poured into ice-water and extracted with EtOAc (100 mL×2). The organic phase was washed, dried and concentrated. The residue was purified by column chromatography to get the title compound (2.2 g). MS (ESI) m/z 134 (M+H+).

Workup

  1. extractionextracted with EtOAc (100 mL×2)
  2. washThe organic phase was washed
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8751eac5577644d588bc9396371a866f
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Linked notes

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