Sulfuric Acid → HCID 18325123, compound

HRID 1250942Notes

Reaction equation

HRID 1250942 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([C:12]3[C:20]4[O:19][CH2:18][O:17][C:16]=4[CH:15]=[CH:14][C:13]=3[NH2:21])=O)[C:4]=2[O:3][CH2:2]1.[CH3:22][O:23][C:24](=[O:29])[C:25](=O)[CH2:26][CH3:27].S(=O)(=O)(O)O>C(O)(=O)C>[O:3]1[C:6]2[CH:7]=[CH:8][C:9]([C:10]3[C:12]4[C:13](=[CH:14][CH:15]=[C:16]5[O:17][CH2:18][O:19][C:20]5=4)[N:21]=[C:25]([C:24]([O:23][CH3:22])=[O:29])[C:26]=3[CH3:27])=[CH:4][C:5]=2[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5451272-Ketobutyric acid methyl esterHCID 18325144HCID 18325144, compound

Product 1

HCID 18325123HCID 18325123, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-1,3-benzodioxole-4-yl 1,3-benzodioxole-4-yl ketone (2.7 g) and 2-ketobutyric acid methyl ester (1.9 g) were dissolved in acetic acid (30 ml), followed by addition of sulfuric acid (0.3 ml). The mixture was refluxed for 1.5 hours and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and water successively, dried over magnesium sulfate and concentrated under reduced pressure to yield the title compound as yellow crystals (2.6 g).

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with aqueous sodium hydrogen carbonate solution and water successively
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a44fade70ac4147a3b2d457f92c069a
Source dataset
uspto-grants-2002_01
Patent number
US06340704B1

Reaction notes

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