Ethyl Acetate → HCID 70303433, compound

HRID 1954064Notes

Reaction equation

HRID 1954064 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[NH:18][C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:22][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].P(Cl)(Cl)(Cl)=O.C(OCC)(=O)C>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:7]([C:19]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:22][CH:21]=3)=[N:18][C@@H:13]3[C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 54451491HCID 54451491, compound2×

Product 1

HCID 70303433HCID 70303433, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

700 mg of (+/-)-cis-N-[2-(3-ethoxy-4-methoxyphenyl)cyclohexyl]-4-sulfamoylbenzamide (compound A1) are dissolved in 100 ml of acetonitrile and 2.0 ml of phosphorus oxychloride and the solution is stirred at 80° C. overnight. The reaction mixture is treated with 60 ml of ethyl acetate and extracted with sodium hydrogencarbonate solution. The organic phase is dried using sodium sulfate and concentrated. The residue is recrystallized from ethanol. 420 mg of the title compound are obtained.

Workup

  1. extractionextracted with sodium hydrogencarbonate solution
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-eb5ae34cd10a477295b95312e09d579d
Source dataset
uspto-grants-2000_09
Patent number
US06121279

Reaction notes

Loading…