Triethylamine → N-(2-azidoethyl)dodecanamide

HRID 384205Notes

Reaction equation

HRID 384205 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]CC)=[N+:2]=[N-:3].N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[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][CH3:18])=[N+:2]=[N-:3]

Participants

5

Reactant 3

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

Product 1

HCID 57914375N-(2-azidoethyl)dodecanamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (0.262 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.103 g, 1.19 mmol) and triethylamine (0.242 g, 2.39 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)dodecanamide (0.220 g, 69%). 1H NMR (300 MHz, CDCl3) δ 6.11 (s, 1H), δ 3.40 (d, 2H), δ 3.37 (d, 2H), δ 2.17 (t, 2H), δ 1.59 (q, 2H), δ 1.22 (s, 14H), δ 0.84 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 173.8, 51.1, 39.1, 36.8, 32.1, 29.8, 29.7, 29.6, 29.5, 29.5, 29.2, 25.9, 22.9, 14.3 ppm; HRMS (ESI) calcd for C14H28N4O (M+) 268.2263, found 268.2259.

Sources & evidence

ORD record
ord-5e0b14c24e754dc3be65344c9c264f75
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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