Phosphorus oxychloride → 2-Methyl-1,3-benzoxazol-6-ol

HRID 2112738Notes

Reaction equation

HRID 2112738 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1/C(=N\O)/C.[CH3:13][C:14]([N:16](C)C)=O.P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:13][C:14]1[O:1][C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=2[N:16]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 516892Sodium BicarbonateHCID 1354004931-(2,4-Dihydroxyphenyl)ethanone oxime

Product 1

HCID 6765042-Methyl-1,3-benzoxazol-6-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cooled (ice-water) solution of (1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime (9.7 g, 57.7 mmol) and dimethylacetamide (11 mL) in acetonitrile (65 mL) was added phosphorous oxychloride (5.6 mL, 60.3 mmol) dropwise. The temperature was not allowed to exceed 10° C. during the reaction. After 1 hour stirring at room temperature the yellow slurry was poured into a mixture of aqueous NaHCO3 and ice. The resulting precipitate was filtered off and dried to give the sub-title compound (6.3 g).

Workup

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

Sources & evidence

ORD record
ord-fc79e2ce2c0d4a0c9b54c6d61c0398b6
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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