Triethylamine → N-(2-azidoethyl)-2,3,4,5,6-pentamethylbenzenesulfonamide

HRID 2283563

Reaction equation

HRID 2283563 reaction equation
[N:1]([CH2:4][CH2:5][NH:6]C(=O)CCCCCCCCCCCCC)=[N+:2]=[N-:3].[CH3:22][C:23]1[C:28]([CH3:29])=[C:27]([CH3:30])[C:26]([CH3:31])=[C:25]([CH3:32])[C:24]=1[S:33](Cl)(=[O:35])=[O:34].N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][S:33]([C:24]1[C:23]([CH3:22])=[C:28]([CH3:29])[C:27]([CH3:30])=[C:26]([CH3:31])[C:25]=1[CH3:32])(=[O:35])=[O:34])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 590180Pentamethylbenzenesulphonyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914412N-(2-azidoethyl)-2,3,4,5,6-pentamethylbenzenesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 2,3,4,5,6-pentamethylbenzene-1-sulfonyl chloride (0.304 g, 1.23 mmol) was reacted with 2-azidoethanamine (0.106 g, 1.23 mmol) and triethylamine (0.249 g, 2.46 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-2,3,4,5,6-pentamethylbenzenesulfonamide (0.296 g, 81%). 1H NMR (300 MHz, CDCl3) δ 5.12 (t, 1H) δ 3.35 (t, 2H), δ 3.05 (q, 2H), 2.59 (s, 6H), δ 2.28 (s, 3H), 2.24 (s, 6H) ppm; 13C NMR (75 MHz, CDCl3) δ 139.9, 136.1, 135.2, 134.2, 51.1, 42.3, 19.2, 17.9, 17.3 ppm; HRMS (ESI) calcd for C13H20N4O2S (M+) 296.1307. Found 296.1304.

Sources & evidence

ORD record
ord-1bbda8b2b6a04addb66dd5618eda1c1b
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Linked notes

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