Triethylamine → HCID 86635088, compound

HRID 384191Notes

Reaction equation

HRID 384191 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].C1(/C=C/CC(Cl)=O)C=CC=CC=1.N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 10856089HCID 10856089, compoundHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 86635088HCID 86635088, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (E)-4-phenylbut-3-enoyl chloride (0.198 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.114 g, 1.19 mmol) and triethylamine (0.239 g, 2.37 mmol) in dichloromethane (5 mL) to give (E)-N-(2-azidoethyl)-4-phenylbut-3-enamide (0.168 g, 55%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, 1H), δ 7.45 (d, 2H), δ 7.29 (m, 3H), δ 7.04 (t, 1H), δ 6.59 (d, 1H), δ 3.55 (q, 2H), δ 3.47 (t, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 166.9, 141.6, 134.9, 130.1, 129.1, 128.1, 120.8, 51.1, 39.4 ppm; HRMS (ESI) calcd for C11H12N4O (M+) 216.1011, found 216.1005.

Sources & evidence

ORD record
ord-69d9c25150ca4ae99e6148c3931b9d80
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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