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Hydroxyamine hydrochloride → HCID 85049509, Verbindung

HRID 226171
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 226171
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[C:9]1([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27](Cl)=[O:28])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[OH:3][NH:2][C:27](=[O:28])[CH:26]=[CH:25][C:22]1[CH:23]=[CH:24][C:19]([S:16](=[O:18])(=[O:17])[NH:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:20][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 73989400HCID 73989400, Verbindung

Produkt 1

HCID 85049509HCID 85049509, VerbindungAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of hydroxylamine hydrochloride (0.21 g, 3.01 mmol) in tetrahydrofuran (4.0 ml) a saturated NaHCO3 solution (2.6 ml) was added and the resultant mixture was stirred at ambient temperature for 25 min. To the reaction mixture a 3-(4-phenylsulfamoyl-phenyl)-acryloyl chloride (44a) (0.19 g, 0.59 mmol) solution in tetrahydrofuran (2.5 ml) was added and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water and saturated NaCl, and the solvent was removed. The residue was washed with diethyl ether to give the title compound (0.074 g, 39%) as white crystals, m.p. 176-177.5° C. 1H NMR (DMSO-d6, HMDSO), δ:6.54 (1H, d, J=−16.0 Hz); 6.96-7.32 (5H, m); 7.47 (1H, d, J=16.0 Hz); 7.76 (4H, s); 9.14 (1 H, br s); 10.29 (1H, br s); 10.86 (1H, s). Anal. Calcd for C15H14N2O4S, %: C 56.59, H 4.43, N 8.80. Found, %: 55.82, H 4.38, N 9.01.

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water and saturated NaCl
  4. customthe solvent was removed
  5. washThe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b22d38d9db8446688c5ba5535864b7e9
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07557140B2

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