Toluene → HCID 86758879, compound

HRID 1861716Notes

Reaction equation

HRID 1861716 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(C)C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C@H:11]1[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]1)[N:17]=[C:18]2[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 54275678HCID 54275678, compound2×

Product 1

HCID 86758879HCID 86758879, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.5 g of (−)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-3,4-dinitrobenzamide (compound A1) are dissolved in 120 ml of acetonitrile or toluene and 3.5 ml of phosphorus oxychloride and the solution is stirred overnight at 80° C. The reaction mixture is concentrated under reduced pressure and the residue is extracted with satd. sodium hydrogencarbonate solution and ethyl acetate. The organic phases are dried using sodium sulfate and concentrated. The residue is recrystallized from ethyl acetate. M.p.: 162-165° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. extractionthe residue is extracted with satd
  3. customThe organic phases are dried
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d2c7635f7dc041919583ce054f14031d
Source dataset
uspto-grants-2003_03
Patent number
US06534518B1

Reaction notes

Loading…