Triethylamine → HCID 57914407, compound

HRID 529930Notes

Reaction equation

HRID 529930 reaction equation
[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CCCCC)=[N+:2]=[N-:3].N([CH2:25][CH2:26]N)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:26][CH:25]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914407HCID 57914407, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (0.242 g, 1.22 mmol) was reacted with 2-azidoethanamine (0.105 g, 1.22 mmol) and triethylamine (0.246 g, 2.43 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-4-butylbenzamide (0.224 g, 75% yield). 1H NMR (300 MHz, CDCl3) δ 7.73 (d, J=8.4 Hz, 2H), δ 7.39 (t, J=1.8 Hz, 1H), δ 7.17 (d, J=8.1 Hz, 2H), δ 3.55 (q, J=8.7, 5.7 Hz, 2H), δ 3.45 (t, J=5.7 Hz, 2H), δ 2.60 (t, J=7.8 Hz, 2H), δ 1.56 (m, 2H), δ 1.30 (m, 2H), δ 0.90 (t, J=4.2 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.5, 147.2, 131.7, 128.8, 127.4, 50.9, 39.7, 35.7, 33.5, 22.5, 14.1 ppm; HRMS (ESI) calcd for C13H18N4O (M+) 246.1481. found 246.1476.

Sources & evidence

ORD record
ord-cbb5909b22054a2394219fa126f7e001
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

Loading…