Triethylamine → HCID 57914398, compound

HRID 2283570Notes

Reaction equation

HRID 2283570 reaction equation
[N:1]([CH2:4][CH2:5][NH:6]C(=O)CCCCCCCCCCCCC)=[N+:2]=[N-:3].[C:22]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 743724-tert-Butylbenzoyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914398HCID 57914398, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 4-tert-butylbenzoyl chloride (0.244 g, 1.23 mmol) was reacted with 2-azidoethanamine (0.106 g, 1.23 mmol) and triethylamine (0.249 g, 2.47 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-4-tert-butylbenzamide (0.221 g, 73%). 1H NMR (300 MHz, CDCl3) δ 7.73 (d, 2H), δ 7.43 (d, 2H), δ 6.95 (t, 1H), δ 3.59 (q, 2H), δ 3.50 (t, 2H), δ 1.31 (s, 9H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.2, 155.4, 131.4, 127.2, 125.8, 51.1, 39.7, 35.2, 31.4 ppm; HRMS (ESI) calcd for C13H18N4O (M+) 246.1480. Found 246.1479.

Sources & evidence

ORD record
ord-3d6a74de231e4729997c1c8e95222aad
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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