Phosphorus oxychloride → HCID 11117191, compound

HRID 1981961Notes

Reaction equation

HRID 1981961 reaction equation
[C:1]([C:5]1[C:6]([OH:16])=[CH:7][C:8]([OH:15])=[C:9](C(=NO)C)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O.C[N:23](C)[C:24](=O)[CH3:25]>C(#N)C>[C:1]([C:5]1[C:6]([OH:16])=[CH:7][C:8]2[O:15][C:24]([CH3:25])=[N:23][C:9]=2[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 136332145HCID 136332145, compound

Product 1

HCID 11117191HCID 11117191, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a mixture of 30 ml of N,N-dimethylacetamide and 30 ml of acetonitrile was dissolved 11 g of 5'-t-butyl-2',4'-dihydroxyacetophenone oxime. To the resulting solution, which was cooled on an ice bath with stirring, was dropwise added 20 ml of phosphorus oxychloride over a period of 30 minutes. The reaction mixture continued to be stirred for an additional 30 minutes as it was and, then, 200 mol of ice water was gradually added thereto over a period of an hour. The crystals thus precipitated were recovered by filtration, and 50 g of 5-t-butyl-2-methyl-6-benzoxazolol (Compound 1) was obtained. Yield 85%, Melting Point 264° to 266° C.

Workup

  1. temperatureTo the resulting solution, which was cooled on an ice bath
  2. customof 30 minutes
  3. stirringto be stirred for an additional 30 minutes as it
  4. waitover a period of an hour
  5. customThe crystals thus precipitated
  6. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-103ae256655d451e83f9b9da7bae6d1c
Source dataset
uspto-grants-1986_06
Patent number
US04594426

Reaction notes

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