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Water → N-(4-Benzoyl-2-methylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

HRID 374872
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 374872
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[NH2:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:18][C:17]=1[CH3:30].O>CN(C)C(=O)C.CCCCCC.C(OCC)C.ClCCl>[C:20]([C:19]1[CH:28]=[CH:29][C:16]([NH:15][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[C:17]([CH3:30])[CH:18]=1)(=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
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Komponenten

8

Edukt 4

HCID 962WaterHCID 21052Benzophenone, 4-amino-3-methyl-HCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

Produkt 1

HCID 9819831N-(4-Benzoyl-2-methylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8058
Hexane
Lösungsmittel
HCID 31374DimethylacetamideLösungsmittel
HCID 21881112Ethyl ether methylene chlorideLösungsmittel

Versuchsvorschrift

To a solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.11 g) in N,N-dimethylacetamide (15 mL) at -20° C. was added thionyl chloride (0.84 g) and the mixture was allowed to stir at -10° to -15° C. for 1 hour. 4-Amino-3-methylbenzophenone (1.00 g) was added in one portion and the reaction mixture was stirred at room temperature overnight. The mixture was poured into water and the resultant gummy solid was collected by filtration. The solid was dissolved in methylene chloride, dried and evaporated to give a brown oil. Chromatography, with diethyl ether:dichloromethane (2:98) as the eluent, gave a white foam which was stirred with hexane for two hours. The title compound was collected by filtration as a white solid (1.04 g); mp 123°-124° C.; MS: m/z=352(M+1); NMR: 1.61 (s,3), 2.28 (s,3), 7.54-7.61 (m,3) 7.66-7.74 (m,6) 9.73 (s,1). Analysis for C18H16F3NO3 : Calculated: C, 61.54; H, 4.59; N, 3.99; Found: C, 61.53; H, 4.73; N, 4.01.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. filtrationthe resultant gummy solid was collected by filtration
  3. dissolutionThe solid was dissolved in methylene chloride
  4. customdried
  5. customevaporated
  6. customto give a brown oil
  7. filtrationThe title compound was collected by filtration as a white solid (1.04 g)

Quellen und Nachweise

ORD-Eintrag
ord-8a01073b36c24dc79dbb4f0545aeedcb
Quelldatensatz
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05482969

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