Triethylamine → N-(2-azidoethyl)thiophene-2-sulfonamide

HRID 2283561Notes

Reaction equation

HRID 2283561 reaction equation
[N:1]([CH2:4][CH2:5][NH:6]C(=O)CCCCCCCCCCCCC)=[N+:2]=[N-:3].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[S:27](Cl)(=[O:29])=[O:28].N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][S:27]([C:23]1[S:22][CH:26]=[CH:25][CH:24]=1)(=[O:29])=[O:28])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 855182-Thiophenesulfonyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914352N-(2-azidoethyl)thiophene-2-sulfonamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, thiophene-2-sulfonyl chloride (0.218 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.103 g, 1.19 mmol) and triethylamine (0.241 g, 2.39 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)thiophene-2-sulfonamide (0.221 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.62 (d, 1H), δ 7.59 (d, 1H), 7.08 (t, 1H), 5.52 (s, 1H), 3.41 (t, 2H), 3.17 (q, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 140.6, 132.7, 132.6, 127.9, 50.9, 42.9 ppm; HRMS (ESI) calcd for C6H8N4O2S2 (M+) 232.0089. Found 232.0084.

Sources & evidence

ORD record
ord-a14842f364424966b594444daa6be8ce
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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