Triethylamine → HCID 57914384, compound

HRID 529933Notes

Reaction equation

HRID 529933 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]CCC)=[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]([C:8]1[CH:9]=[CH:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:26][CH:25]=1)=[O:21])=[N+:2]=[N-:3]

Participants

5

Reactant 3

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

Product 1

HCID 57914384HCID 57914384, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (0.283 g, 1.31 mmol) was reacted with 2-azidoethanamine (0.113 g, 1.31 mmol) and triethylamine (0.264 g, 2.61 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)biphenyl-4-carboxamide (0.297 g, 85% yield). 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H), δ 7.67 (m, 4H), δ 7.44 (m, 3H), δ 6.63 (s, 1H), δ 3.67 (q, J=6.0, 1.8 Hz, 2H), δ 3.58 (t, J=6.0 Hz, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 167.8, 144.8, 140.1, 132.9, 129.2, 128.3, 127.8, 127.5, 127.4, 51.2, 39.7 ppm; HRMS (ESI) calcd for C15H14N4O (M+) 266.1168. found 266.1162.

Sources & evidence

ORD record
ord-180b97b873d9426faacf3df3fdea7a13
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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