Benzoyl chloride → HCID 23497778, compound

HRID 1837150Notes

Reaction equation

HRID 1837150 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:12]([CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[CH2:13][CH3:14])[CH3:11]>N1C=CC=CC=1.ClCCl>[CH2:13]([N:12]([CH2:10][CH3:11])[CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:22][CH:23]=1)[CH3:14]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 191331HCID 191331, compound

Product 1

HCID 23497778HCID 23497778, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Benzoylchloride (6.33 g, 45 mmol) in pyridine (50 mL) was added over a 15-minute period to a solution of N,N-diethyl-3-(p-nitrophenyl)-propylamine (9.4 g, 45 mmol) in pyridine (50 mL). The solution was refluxed for 1.5 hours. The solvent was evaporated, giving a brown oil. The oil was dissolved in dichloromethane (300 mL) and washed with 1N NaOH (200 mL). The dichloromethane layer was dried and evaporated. Toluene (100 mL) was added to the resulting oil and re-evaporated. The semi-solid residue was washed with pentane, then recrystalized from cyclohexane (125 mL) to give the title compound.

Workup

  1. temperatureThe solution was refluxed for 1.5 hours
  2. customThe solvent was evaporated
  3. customgiving a brown oil
  4. washwashed with 1N NaOH (200 mL)
  5. dry with materialThe dichloromethane layer was dried
  6. customevaporated
  7. additionToluene (100 mL) was added to the resulting oil
  8. customre-evaporated
  9. washThe semi-solid residue was washed with pentane
  10. customrecrystalized from cyclohexane (125 mL)

Sources & evidence

ORD record
ord-4d7b3078df9f440d828b9f7f940d2d66
Source dataset
uspto-grants-2004_08
Patent number
US06780883B2

Reaction notes

Loading…