Acetonitrile → 2-Methyl-1,3-benzoxazol-6-ol

HRID 270085Notes

Reaction equation

HRID 270085 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1/C(=N\O)/C.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+].[C:23](#[N:25])[CH3:24]>CC(N(C)C)=O>[CH3:24][C:23]1[O:1][C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=2[N:25]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1354004931-(2,4-Dihydroxyphenyl)ethanone oxime

Product 1

HCID 6765042-Methyl-1,3-benzoxazol-6-olYield 73%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a cooled (5° C.) solution of (1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime (9.7 g, 57.7 mmol) in acetonitrile (65 mL) and dimethylacetamide (11 mL) was added phosphorus oxychloride (5.6 mL, 60.3 mmol) drop wise. The temperature was not allowed to exceed 10° C. during the addition. After 1 hrs stirring at room temperature the yellow slurry was poured on a mixture of sodium hydrogen carbonate and ice. The resulting precipitate was filtered off and dried yielding 6.3 g (73%) the titled compound.

Workup

  1. additionto exceed 10° C. during the addition
  2. filtrationThe resulting precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-e54980c59e814b719131e7402bc7f22d
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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