Triethylamine → HCID 86659554, compound

HRID 529936Notes

Reaction equation

HRID 529936 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][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[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:26]=[CH:25][C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

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

Product 1

HCID 86659554HCID 86659554, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (0.383 g, 1.43 mmol) the acid chloride was reacted with 2-azidoethanamine (0.124 g, 1.43 mmol) and triethylamine (0.290 g, 2.87 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-4-nonylbenzamide (0.441 g, 97% yield). 1H NMR (300 MHz, CDCl3) δ 7.72 (d, 2H), δ 7.26 (t, 1H), δ 7.18 (d, 2H), δ 3.57 (q, 2H), δ 3.45 (t, 2H), δ 2.60 (t, 2H), δ 1.58 (m, 2H), δ 1.27 (m, 12H), δ 0.86 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.5, 147.3, 131.7, 128.8, 127.4, 50.9, 39.7, 36.1, 32.1, 31.5, 29.8, 29.7, 29.6, 29.5, 22.9, 14.4 ppm; HRMS (ESI) calcd for C18H28N4O (M+) 316.2263. found 316.2268.

Sources & evidence

ORD record
ord-c4c8744e82334b3dbae977864e84d419
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

Loading…