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Triethylamine → 1,2-Dihydro-8-(4-(methylsulphonyl)piperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxide

HRID 2309692
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2309692
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]1([C:19]2[C:20]3[N:21]([CH2:36][CH2:37][N:38]=3)[C:22]3[C:27]([N+:28]=2[O-:29])=[CH:26][CH:25]=[C:24]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:23]=3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH3:1][S:2]([N:33]1[CH2:34][CH2:35][N:30]([C:24]2[CH:23]=[C:22]3[C:27]([N+:28]([O-:29])=[C:19]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:20]4[N:21]3[CH2:36][CH2:37][N:38]=4)=[CH:26][CH:25]=2)[CH2:31][CH2:32]1)(=[O:4])=[O:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 99501581,2-Dihydro-4-phenyl-8-piperazinylimidazo[1,2-a]quinoxaline 5-oxide

Produkt 1

HCID 139586181,2-Dihydro-8-(4-(methylsulphonyl)piperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxideAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A solution of methanesulfonyl chloride (0.33 g, 0.003 mol) in dichloromethane (20 ml) was cooled in an ice-bath. To this solution was added dropwise with stirring, a solution of triethylamine (0.29 g, 0.003 mol) and 1,2-dihydro-4-phenyl-8-piperazinylimidazo[1,2-a]quinoxaline 5-oxide (1 g, 0.003 mol) in dichloromethane (10 ml). The reaction mixture was stirred for an additional 15 minutes and then was allowed to warm to room temperature. The reaction mixture was washed with water, dried over anhydrous magnesium sulphate and then evaporated to dryness under reduced pressure to yield a yellow solid. Recrystallization from ethyl acetate yielded 1,2-dihydro-8-(4-(methylsulphonyl)piperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxide (0.8 g), as yellow crystals, m.p. 252°-253° C. (Found: C,59.19; H,5.35; N,16.33%; C21H23N5O3S requires C,59.29; H,5.41; N,16.47%) having the formula: ##STR31##

Aufarbeitung

  1. additionTo this solution was added dropwise
  2. stirringThe reaction mixture was stirred for an additional 15 minutes
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customto yield a yellow solid
  7. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-aee75739d7a44804a0cf00254b452c24
Quelldatensatz
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04696928

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