Ozone → 3-[5-tert-Butyl-3-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone

HRID 2417902Notes

Reaction equation

HRID 2417902 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([N:13]([CH2:15][CH:16]=C)[CH3:14])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:18]=[O+][O-]>CO>[C:1]([C:5]1[O:9][N:8]=[C:7]([N:10]2[CH:16]([OH:18])[CH2:15][N:13]([CH3:14])[C:11]2=[O:12])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 24823OzoneHCID 13373599N'-(5-tert-Butyl-1,2-oxazol-3-yl)-N-methyl-N-prop-2-en-1-ylurea

Product 1

HCID 1569093-[5-tert-Butyl-3-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4.74 g. portion of 1-(5-t-butylisoxazol-3-yl)-3-allyl-3-methylurea was dissolved in 50 ml. of methanol, and was cooled to -12°. Ozone-containing air was bubbled through the mixture with good stirring for 80 minutes. The temperature rose as high as 0° during the ozone addition, and the mixture foamed and left solids on the flask walls above the liquid. It was necessary to wash the solid down with 20 ml. of additional methanol. Ten ml. of additional methanol was used to wash the gas frit when it began to plug from precipitated product. After the addition was complete, nitrogen was bubbled through the solution for 5 minutes, and then 1.5 ml. of dimethyl sulfide was added and the mixture was warmed to 20° and diluted with 80 ml. of water. The methanol was removed under vacuum at 40°, and the remaining mixture was filtered and the solids were washed with 50 ml. of water and dried under vacuum at 50° to obtain 2.68 g. of the desired product, m.p. 173°-176°. It was further identified by nmr analysis which showed it to be substantially identical to the product of Example 1.

Workup

  1. customwas bubbled through the mixture
  2. additionThe temperature rose as high as 0° during the ozone addition
  3. waitleft solids on the flask walls above the liquid
  4. washto wash the solid down with 20 ml
  5. washto wash the gas frit when it
  6. customfrom precipitated product
  7. additionAfter the addition
  8. customnitrogen was bubbled through the solution for 5 minutes
  9. additionof dimethyl sulfide was added
  10. temperaturethe mixture was warmed to 20°
  11. additiondiluted with 80 ml
  12. customThe methanol was removed under vacuum at 40°
  13. filtrationthe remaining mixture was filtered
  14. washthe solids were washed with 50 ml
  15. dry with materialof water and dried under vacuum at 50°
  16. customto obtain 2.68 g

Sources & evidence

ORD record
ord-b0c1208544184b89a5672de57610cb4d
Source dataset
uspto-grants-1984_09
Patent number
US04471123

Reaction notes

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