Triethylamine → HCID 86659555, compound

HRID 529937Notes

Reaction equation

HRID 529937 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]C)=[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][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[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 86659555HCID 86659555, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (0.262 g, 1.19 mmol) the acid chloride 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)-4-octylbenzamide (0.220 g, 69% yield). 1H NMR (300 MHz, CDCl3) δ 7.73 (d, 2H), δ 7.37 (t, 1H), δ 7.17 (d, 2H), 63.56 (q, 2H), δ 3.44 (t, 2H), δ 2.59 (t, 2H), δ 1.58 (m, 2H), δ 1.27 (m, 10H), 60.86 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.4, 147.3, 131.7, 128.8, 127.4, 50.9, 39.7, 36.1, 32.1, 31.5, 29.7, 29.5, 29.5, 22.9, 14.3 ppm; HRMS (ESI) calcd for C17H28N4O (M+) 302.2107. found 302.2104.

Sources & evidence

ORD record
ord-d6a792787fb446e1a968289dd1d89b4c
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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