Triethylamine → N-(3-bromopropyl)-3-cyano-benzenesulfonamide

HRID 1182090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182090
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].CN(C1C=CC=CN=1)C.[C:16]([C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1)#[N:17].C(N(CC)CC)C>ClCCl>[Br:2][CH2:3][CH2:4][CH2:5][NH:6][S:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]#[N:17])[CH:19]=1)(=[O:26])=[O:25]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 787013-Bromopropylamine hydrobromideHCID 28013603-Cyanobenzene-1-sulfonyl chloride

Produkt 1

HCID 43133728N-(3-bromopropyl)-3-cyano-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A suspension of bromopropylamine hydrogen bromide (0.219 g, 1 mmol) in dichloromethane (2 ml) is treated with a solution of dimethylaminopyridine (0.004 g) in dichloromethane (0.5 ml) followed by a solution of 3-cyano-benzenesulfonyl chloride (0.2 g, 1.0 mmol) in dichloromethane (0.5 ml). Triethylamine (0.3 ml, 2.16 mmol) is added and the reaction mixture stirred at ambient temperature for 2 hours, then quenched with water and saturated aqueous NaHCO3, and extracted into dichloromethane. The organic phase is washed with aqueous 1M HCl solution and brine, dried over MgSO4 and evaporated to afford crude N-(3-bromopropyl)-3-cyano-benzenesulfonamide. (13C NMR, 100 MHz, CDCl3, 30.2, 32.6, 41.9, 114.3, 117.5, 130.7, 130.9, 131.1, 136.3, 142.1).

Aufarbeitung

  1. customquenched with water and saturated aqueous NaHCO3
  2. extractionextracted into dichloromethane
  3. washThe organic phase is washed with aqueous 1M HCl solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-73583611340749848866c9605af5837b
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288537B2

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