Triethylamine → HCID 57914360, compound

HRID 2283568Notes

Reaction equation

HRID 2283568 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].C(Cl)(=O)CCCCCCCCC.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][CH3:16])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 66982Decanoyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914360HCID 57914360, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, decanoyl chloride (0.251 g, 1.32 mmol) was reacted with 2-azidoethanamine (0.114 g, 1.32 mmol) and triethylamine (0.267 g, 2.64 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl) decanamide (0.262 g, 83%). 1H NMR (300 MHz, CDCl3) δ 6.49 (s, 1H), δ 3.36 (s, 2H), δ 3.35 (s, 2H), δ 2.14 (t, 2H), δ 1.46 (m, 2H), δ 1.21 (m, 12H), δ 0.81 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 174.1, 50.9, 39.1, 36.8, 32.0, 29.7, 29.6, 29.5, 29.4, 25.9, 22.8, 14.3 ppm; HRMS (ESI) calcd for C12H24N4O (M+) 240.1950. Found 240.1947.

Sources & evidence

ORD record
ord-d5d9445a2c034bde8500c0ca0ae96b48
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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