Benzenesulfonyl chloride → N-(2-azidoethyl)benzenesulfonamide

HRID 384190Notes

Reaction equation

HRID 384190 reaction equation
[N:1]([CH2:4][CH2:5][NH:6]C(=O)CCCCCCCCCCCCC)=[N+:2]=[N-:3].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][S:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:30])=[O:29])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914390N-(2-azidoethyl)benzenesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, benzenesulfonyl chloride (0.201 g, 1.16 mmol) was reacted with 2-azidoethanamine (0.100 g, 1.16 mmol) and triethylamine (0.235 g, 2.32 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)benzenesulfonamide (0.289 g, 84%). 1H NMR (300 MHz, CDCl3) δ 7.90 (d, 2H), δ 7.55 (m, 3H), δ 5.47 (s, 1H), δ 3.39 (t, 2H), δ 3.12 (t, 2H) ppm; 13C NMR (75 MHz, CDCl3) 139.8, 133.2, 129.5, 127.2, 50.9, 42.6 ppm; HRMS (ESI) calcd for C6H8N4O2S (M+) 226.0524, found 226.0523.

Sources & evidence

ORD record
ord-d154b0dac45a4099b9334fd20a0c5073
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

Loading…