Ethyl Acetate → HCID 19003244, compound

HRID 2259268Notes

Reaction equation

HRID 2259268 reaction equation
[C:1]([NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1]([NH:5][C:6](=[S:26])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 591441N-tert-Butyl-4-nitrobenzamide

Product 1

HCID 19003244HCID 19003244, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The preparation of Example 1 was repeated with the changes that N-tert-butyl 4-nitrobenzamide (3.00 g, 0.0135 mole) and 2,4-bis (4-methoxyphenyl) -1,3 -dithia-2,4-diphosphetane-2,4-disulfide (3.28 g, 0.0081 mole) were the starting reactants and the reaction was carried out by refluxing in 50 mL dry toluene solvent for 3 hours. In addition, the solvent was removed in vacuo leaving a yellow viscous oil. The oil was taken up into ethyl acetate and the solution filtered through silica gel. The solvent was removed in vacuo, the residue taken up into ethanol, and the mixture filtered through fluted filter paper. Recrystallization from ethanol produced 2.20 g golden crystals of the desired product (68% yield), mp 136°-138° C. Proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 8.21 ppm (d, 8.0 Hz, 2H; 3,5-aryl H); 7.76 ppm (d, 8.0 Hz, 2H; 2,6-aryl H); 1.67 ppm (s, 9H; tert-butyl H).

Workup

  1. customThe preparation of Example 1
  2. customIn addition, the solvent was removed in vacuo
  3. customleaving a yellow viscous oil
  4. filtrationthe solution filtered through silica gel
  5. customThe solvent was removed in vacuo
  6. filtrationthe mixture filtered
  7. filtrationthrough fluted filter paper
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-54004d1ba18c4141a8832420495c2299
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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