Benzoyl chloride → Benzamide, N-propyl-

HRID 2381565Notes

Reaction equation

HRID 2381565 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([NH2:13])[CH2:11][CH3:12]>C(Cl)Cl>[CH2:10]([NH:13][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 7852Propylamine

Product 1

HCID 25354Benzamide, N-propyl-Yield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dry DCM (30 mL) was added to benzoyl chloride (2.06 mL, 17.7 mmol) followed by the dropwise addition of propylamine (3.19 mL, 38.9 mmol) over 5 min at 0° C. The system was stirred at 0° C. under nitrogen for 1 h and monitored by TLC. After 1 h the system was washed with 1M HCl (20 mL), brine (10 mL) and dried with MgSO4. The solvent was removed to give N-Propylbenzamide as a white solid (2.6 g, 15.9 mmol, 90%); Rf 0.38 (40:60 EtOAc:petrol). mp 87.6-88.9° C. Lit. 83-84° C.7 1H NMR: (300 MHz, CDCl3) δ 0.90 (t, 3H, J=7.4 Hz, CH2—CH2—CH3), 1.56 (sex, 2H, J=7.2 Hz, N—CH2—CH2), 3.33 (m, 2H, N—CH2), 6.21 (bs, 1H, NH), 7.31-7.43 (m, 3H, Ar—H), 7.69 (m, 2H, Ar—H). 13C NMR: (75 MHz, CDCl3) δ 11.8, 23.3, 42.1, 127.2, 128.8, 131.6, 135.2, 167.9. LC/MS-ES+ m/z 164.2 [MH+], 327.1, 328.1.

Workup

  1. washAfter 1 h the system was washed with 1M HCl (20 mL), brine (10 mL)
  2. dry with materialdried with MgSO4
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-f50bcab39e62407e9d46199f93bf573f
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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