Acetic Acid → HCID 18331404, compound

HRID 2270556Notes

Reaction equation

HRID 2270556 reaction equation
[C:1]([C:3]1([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[CH2:21][CH3:22])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)#[N:2].C(O)(=[O:25])C.S(=O)(=O)(O)O>O>[CH2:21]([C:13]1[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[C:3]1([C:1]([NH2:2])=[O:25])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 18331406HCID 18331406, compound

Product 1

HCID 18331404HCID 18331404, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of the compound (1.16 g) obtained in Example 25b and acetic acid (10 ml), water (2 ml) and concentrated sulfuric acid (20 ml) were added sequentially. The reaction mixture was heated under reflux for 13 h, cooled, put into ice water and subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (870 mg) (yield, 71%).

Workup

  1. additionwere added sequentially
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 13 h
  4. temperaturecooled
  5. extractionsubjected to extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5dafd1d390e4de6824f34ddd201bb5a
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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