Sulfuric Acid → HCID 13576503, compound

HRID 638572Notes

Reaction equation

HRID 638572 reaction equation
C([O:4][C:5](=[O:22])[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12](=[O:21])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:8]=1)(C)C.OS(O)(=O)=O>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([C:9]2[N:8]=[C:7]([CH2:6][C:5]([OH:22])=[O:4])[O:11][N:10]=2)=[O:21])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 13576498HCID 13576498, compound

Product 1

HCID 13576503HCID 13576503, compoundYield 94.6%

Procedure

Finely powdered isopropyl[3-(4-methoxybenzoyl)-1,2,4-oxadiazol-5-yl]acetate (13.5 g) was added in portions over 15 minutes to concentrated H2SO4 (1000 ml) with mechanical stirring. The mixture was stirred an additional 15 minutes until the ester dissolved. The resulting solution was added slowly to ice water (6 liters) with stirring. The precipitated solid was filtered and dissolved in Et2O (1500 ml). The organic phase was washed with water until neutral, saturated NaCl, dried over Na2SO4, and concentrated in vacuo to give 11.0 g of an amorphous solid. The crude acid (7.7 g) was triturated with boiling Et2O (500 ml) to give 3.6 g (45%) of a powder, m.p. 126°-127°.

Workup

  1. dissolutiondissolved
  2. filtrationThe precipitated solid was filtered
  3. dissolutiondissolved in Et2O (1500 ml)
  4. washThe organic phase was washed with water until neutral, saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fb0fffaef3445019651c8328efcf474
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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