Triethylamine → HCID 57914406, compound

HRID 529932Notes

Reaction equation

HRID 529932 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]CCCC)=[N+:2]=[N-:3].[CH2:22](C1C=CC(C(Cl)=O)=CC=1)[CH2:23]CCC.N(CCN)=[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][CH3:16])=[CH:23][CH:22]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 1708124-Pentylbenzoyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914406HCID 57914406, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 4-pentylbenzoyl chloride (0.283 g, 1.35 mmol) was reacted with 2-azidoethanamine (0.116 g, 1.35 mmol) and triethylamine (0.273 g, 2.69 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-4-pentylbenzamide (0.267 g, 76% yield). 1H NMR (300 MHz, CDCl3) δ 7.74 (d, J=8.1 Hz, 2H), δ 7.61 (t, J=5.1 Hz, 1H), δ 7.15 (d, J=8.4 Hz, 2H), δ 3.54 (q, J=5.7, 5.1 Hz, 2H), δ 3.44 (t, J=5.7 Hz, 2H), δ 2.58 (t, J=7.5 Hz, 2H), δ 1.57 (m, 2H), δ 1.26 (m, 4H), δ 0.86 (t, J=6.6 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.6, 147.2, 131.7, 128.7, 127.5, 50.8, 39.7, 35.9, 31.6, 31.1, 22.7, 14.2 ppm; HRMS (ESI) calcd for C14H20N4O (M+) 260.1637. found 260.1632.

Sources & evidence

ORD record
ord-5c32824978494535a7e496c1b99b2ced
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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