3-Oxo-3-phenylpropionanilide → 3-Deoxyviridicatin

HRID 2380327Notes

Reaction equation

HRID 2380327 reaction equation
[C:1]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>S(=O)(=O)(O)O.O>[C:2]1([C:1]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:10](=[O:11])[CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 703983-Oxo-3-phenylpropionanilide

Product 1

HCID 3759123-Deoxyviridicatin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Benzoylacetanilide (150 g) (prepared according to the method of Brown et al., J. Am. Chem. Soc., 79, 2919, (1957)) in concentrated sulphuric acid (76%) (130 cc) is heated for 4 hours at 100° C. The reaction mixture is slowly poured with stirring in distilled water (3150 cc). The precipitate obtained is filtered, washed with water and then with acetone, and dried at 40° C. under reduced pressure. The residue obtained is recrystallised in ethanol. (white solid; m.p.=268°-269° C.)

Workup

  1. additionThe reaction mixture is slowly poured
  2. customThe precipitate obtained
  3. filtrationis filtered
  4. washwashed with water
  5. dry with materialwith acetone, and dried at 40° C. under reduced pressure
  6. customThe residue obtained
  7. customis recrystallised in ethanol

Sources & evidence

ORD record
ord-e30dd51f81844c29b3ea24c2216b37f3
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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