Water → (2R)-3-bromo-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

HRID 133736

Reaktionsgleichung

Reaktionsgleichung von HRID 133736
S(Cl)(Cl)=O.[Br:5][CH2:6][C@@:7]([OH:12])([CH3:11])[C:8](O)=[O:9].[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[NH2:17].O>CC(N(C)C)=O>[Br:5][CH2:6][C@@:7]([OH:12])([CH3:11])[C:8]([NH:17][C:16]1[CH:18]=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[C:14]([CH3:13])[CH:15]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 118984-Nitro-m-toluidineHCID 24386Thionyl ChlorideHCID 10582468(2R)-3-BROMO-2-HYDROXY-2-METHYLPROPANOIC ACID

Produkt 1

HCID 59903827(2R)-3-bromo-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

Thionyl chloride (0.48 ml, 6.6 mmol) was added dropwise to a solution of (2R)-3-Bromo-2-hydroxy-2-methylpropionic acid (1.0 g, 5.5 mmol) in 10 ml of DMA at −5 to −10° C. The mixture was stirred for 2 h, and a solution of 3-methyl-4-nitroaniline (0.83 g, 5.5 mmol) in 7 ml of DMA was added to the above mixture. The resulting mixture was stirred for 3 h at room temperature and poured into water (250 ml). The aqueous phase was extracted with ethyl acetate (4×50 ml), dried over Na2SO4 and evaporated. The yield of the desired compound was 2.5 g (contains also DMA), and it was used without further purifications. 1H NMR (DMSO-d6): 1.48 (3H, s), 2.53 (3H, s), 3.58 (1H, d, J=10.4 Hz), 3.82 (1H, d, J=10.4 Hz), 6.34 (1H, bs), 7.86 (1H, dd, J=9.0 Hz and 2.2 Hz), 7.91 (1H, d, J=2.2 Hz), 8.04 (1H, d, J=9.0 Hz), 10.09 (1H, bs).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 3 h at room temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate (4×50 ml)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ec963901cf894fa89b434d4ad825b1a6
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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