Triethylamine → HCID 57914349, compound

HRID 598673Notes

Reaction equation

HRID 598673 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].[CH2:22](C1C=CC(C(Cl)=O)=CC=1)[CH2:23]CCCCC.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][CH2:16][CH2:17][CH3:18])=[CH:23][CH:22]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 1708644-Heptylbenzoyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914349HCID 57914349, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 4-heptylbenzoyl chloride (0.289 g, 1.21 mmol) was reacted with 2-azidoethanamine (0.104 g, 1.21 mmol) and triethylamine (0.245 g, 2.42 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-4-heptylbenzamide (0.260 g, 75%). 1H NMR (300 MHz, CDCl3) δ 7.73 (d, 2H), δ 7.19 (d, 3H), δ 3.57 (q, 2H), δ 3.47 (t, 2H), δ 2.61 (t, 2H), δ 1.61 (m, 2H), δ 1.26 (m, 8H), δ 0.87 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.3, 147.3, 131.7, 128.8, 127.4, 50.9, 39.7, 36.1, 32.0, 31.4, 29.4, 29.3, 22.9, 14.3 ppm; HRMS (ESI) calcd for C16H24N4O (M+) 288.1950. found 288.1943.

Sources & evidence

ORD record
ord-3c5fbd04eb4e498c916a2b7379d0c8ee
Source dataset
uspto-grants-2011_03
Patent number
US07897631B2

Reaction notes

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