Ethyl Acetate → HCID 178458844, compound

HRID 477408Notes

Reaction equation

HRID 477408 reaction equation
[O-:1][C:2]#[N:3].[K+].[C:5]([C:9]1[C:10](=[O:26])[CH2:11][CH:12]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([NH2:24])[C:17]=2[CH3:25])[CH2:13][C:14]=1[OH:15])(=[O:8])[CH2:6][CH3:7].C(OCC)(=O)C>O.C(O)(=O)C>[C:5]([C:9]1[C:10](=[O:26])[CH2:11][CH:12]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([NH:24][C:2]([NH2:3])=[O:1])[C:17]=2[CH3:25])[CH2:13][C:14]=1[OH:15])(=[O:8])[CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11378442Potassium cyanateHCID 178458842HCID 178458842, compound

Product 1

HCID 178458844HCID 178458844, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of potassium cyanate (0.54 g, 6.66 mmol) in water (3 ml) was added cautiously to a solu tion of 2-propionyl-3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.0 g, 3.32 mmol) in acetic acid (9 ml) and water (3.2 ml). Stirring was continued for 1 hr then allowed to stand for 15 hr. Water and ethyl acetate were added. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to yield 2-propionyl-3-hydroxy-5-(3-ureido-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a brown semi solid (0.96 g, 84%). The compound was characterized by proton magnetic resonance spectroscopy (CDCl3, δ in ppm): 1.11 (3H,t); 2.20 (3H,s); 2.32 (6H,s); 2.4-4.1 (7H,m); 5.12 (2H,brs); 6.82 (1H,s); 7.25 (1H,brs).

Workup

  1. waitto stand for 15 hr
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eb101ad1224549a6880941cd2351d0df
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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