Sulfuric Acid → HCID 13576499, compound

HRID 638568Notes

Reaction equation

HRID 638568 reaction equation
C([O:4][C:5](=[O:20])[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1)(C)C.S(=O)(=O)(O)O>>[C:12]([C:9]1[N:8]=[C:7]([CH2:6][C:5]([OH:20])=[O:4])[O:11][N:10]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 13809948HCID 13809948, compound

Product 1

HCID 13576499HCID 13576499, compoundYield 48.1%

Procedure

To a flask containing 8.6 g of isopropyl(3-benzoyl-1,2,4-oxadiazol-5-yl)acetate, which had been cooled in an ice bath, was added 50 ml of cold 97% sulfuric acid. This mixture was swirled continuously for three minutes. The resultant solution was poured gradually into one liter of ice water with mechanical stirring to precipitate the product. The solid was collected by filtration, washed with excess water and dried in vacuo. Recrystallization from acetone/hexane gave 3.5 g (48%) of crystals, m.p. 143°-144.5°.

Workup

  1. temperaturehad been cooled in an ice bath
  2. customto precipitate the product
  3. filtrationThe solid was collected by filtration
  4. washwashed with excess water
  5. customdried in vacuo
  6. customRecrystallization from acetone/hexane

Sources & evidence

ORD record
ord-4eb7aea7a6144fc28080d860557eca0a
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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