Propylamine → 3-iodo-N-propylbenzamide

HRID 2421610Notes

Reaction equation

HRID 2421610 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH2:11]([NH2:14])[CH2:12][CH3:13]>>[CH2:11]([NH:14][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=1)[CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 7852PropylamineHCID 120603-Iodobenzoic acid

Product 1

HCID 34091083-iodo-N-propylbenzamideYield 82%

Procedure

Using Preparation Method 1, 3-iodobenzoic acid was reacted with n-propylamine. The resulting reaction mixture was purified using SiO2 with CH2Cl2/petroleum ether 95:5 to CH2Cl2/AcOEt 95:5 to give N-n-propyl-3-iodobenzamide as an off-white solid (82%). NMR 1H (ppm, CDCl3): 8.07 (t, J4=1.6 Hz, 1H), 7.80 (d. t., J3=7.9 Hz, J4=1.1 Hz, 1H), 7.69 (d. t., J3=7.8 Hz, J4=1.1 Hz, 1H), 7.15 (t, J3=7.8 Hz, 1H), 6.06 (br. s., 1H), 3.43-3.36 (m, 2H), 1.62 (sext., J3=7.3 Hz, 2H), 0.97 (t, J3=7.4 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-eba5254a619a46e9b2397ca374d26c04
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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