Benzoyl chloride → Benzamide, N-propyl-

HRID 2421607Notes

Reaction equation

HRID 2421607 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:17]([NH2:20])[CH2:18][CH3:19]>C(Cl)Cl>[CH2:17]([NH:20][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7852PropylamineHCID 8471Triethylamine

Product 1

HCID 25354Benzamide, N-propyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzoyl chloride (116 μL, 1 mmol) in 1 mL of dry CH2Cl2 was treated successively at 0° C. with triethylamine (167 μL, 1.2 mmol) and n-propylamine (124 μL, 1.5 mmol). The reaction was stirred at room temperature for two hours. The resulting reaction mixture was diluted with CH2Cl2 washed with 2M HCl, followed by saturated NaHCO3, then brine. The resulting solution was then dried over MgSO4. The residue was purified using SiO2 with CH2Cl2/Petroluem ether 95:5 to CH2Cl2 100%. A white solid was obtained (166 mg, quantitative yield). NMR 1H (ppm, CDCl3): 7.74 (d, J3=8.1 Hz, 2H), 7.41 (t. t., J3=7.2 Hz, J4=1.3 Hz, 1H), 7.33 (t. t., J3=7.6 Hz, J4=1.6 Hz, 2H), 5.23 (br. s., 1H), 3.36-3.30 (m, 2H), 1.57 (sext., J3=7.2 Hz, 2H), 0.90 (t, J3=7.4 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 2M HCl
  3. dry with materialThe resulting solution was then dried over MgSO4
  4. customThe residue was purified
  5. customA white solid was obtained (166 mg, quantitative yield)

Sources & evidence

ORD record
ord-562bce96483b4e38bde5d99863d6ffd6
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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