Triethylamine → HCID 55136529, compound

HRID 529925Notes

Reaction equation

HRID 529925 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]CCCCCCC)=[N+:2]=[N-:3].[I:22]C1C=CC=CC=1C(Cl)=O.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][CH:11]=[CH:12][C:13]=1[I:22])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 691122-Iodobenzoyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 55136529HCID 55136529, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 2-iodobenzoyl chloride (0.312 g, 1.17 mmol) was reacted with 2-azidoethanamine (0.101 g, 1.17 mmol) and triethylamine (0.237 g, 2.34 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-2-iodobenzamide (0.272 g, 74% yield). 1H NMR (300 MHz, CDCl3) δ 7.84 (d, J=7.2 Hz, 1H), δ 7.33 (m, 2H), S 7.08 (t, J=3.3 Hz, 1H), δ 6.51 (s, 1H), δ 3.54 (s, 2H), δ 3.53 (s, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 169.9, 141.9, 140.0, 131.5, 128.4, 128.4, 92.7, 50.8, 39.6 ppm; HRMS (ESI) calcd for C9H91N4O (M+) 315.9821. found 315.9820.

Sources & evidence

ORD record
ord-f5792d26873540b1ad25f13c37ccc504
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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