Triethylamine → N-(2-azidoethyl)-3,5-difluorobenzamide

HRID 529927Notes

Reaction equation

HRID 529927 reaction equation
[N:1]([CH2:4][CH2:5][NH:6]C(=O)CCCCCCCCCCCCC)=[N+:2]=[N-:3].[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([F:32])[CH:31]=1)[C:26](Cl)=[O:27].N(CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:26](=[O:27])[C:25]1[CH:24]=[C:23]([F:22])[CH:31]=[C:30]([F:32])[CH:29]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 1456003,5-Difluorobenzoyl chlorideHCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 55136734N-(2-azidoethyl)-3,5-difluorobenzamideYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 3,5-difluorobenzoyl chloride (0.219 g, 1.24 mmol) was reacted with 2-azidoethanamine (0.107 g, 1.24 mmol) and triethylamine (0.251 g, 2.48 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-3,5-difluorobenzamide (0.280 g, 59% yield). 1H NMR (300 MHz, CDCl3) δ 7.32 (s, 2H), 7.29 (s, 1H), 6.91 (t, J=2.4 Hz, 1H), 3.58 (q, J=5.7, 5.1 Hz, 2H), 3.51 (t, J=4.8 Hz, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 165.9, 164.7, 161.5, 161.4, 137.6, 110.7, 106.9, 50.7, 39.9 ppm; HRMS (ESI) calcd for C9H8F2N4O2S (M+) 226.0666. found 226.0662.

Sources & evidence

ORD record
ord-9d7e4160319f482eb323aaec9e01c5fe
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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