Phosphorus oxychloride → HCID 70089088, compound

HRID 2187505Notes

Reaction equation

HRID 2187505 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]([C:26]#[N: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(=O)([O-])O.[Na+]>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]([C:26]#[N: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 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 53848462HCID 53848462, compound2×

Product 1

HCID 70089088HCID 70089088, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.1 g of (+/−)-cis-N-[2-(3-ethoxy-4-methoxyphenyl)-cyclohexyl]-4-cyanobenzamide (compound A5) are dissolved in 100 ml of acetonitrile and 3 ml of phosphorus oxychloride and the solution is stirred at 50° C. for 8 h. The reaction mixture is added to 100 ml of saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase is washed with sodium hydrogencarbonate solution and water, dried using sodium sulfate and concentrated. 4.3 g of the title compound are obtained as solidified oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with sodium hydrogencarbonate solution and water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a29b7a6c336043be86d3611df066e539
Source dataset
uspto-grants-2002_06
Patent number
US06410551B1

Reaction notes

Loading…