Dimethylformamide → HCID 20064752, Verbindung

HRID 359298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359298
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Br:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br.[CH3:21][C:22]([NH:25][C:26]1[O:27][C:28]([C:35]([OH:37])=[O:36])=[C:29]([C:31]([F:34])([F:33])[F:32])[N:30]=1)([CH3:24])[CH3:23]>O>[CH3:24][C:22]([NH:25][C:26]1[O:27][C:28]([C:35]([O:37][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[Br:12])=[O:36])=[C:29]([C:31]([F:32])([F:34])[F:33])[N:30]=1)([CH3:21])[CH3:23]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 769652-Bromobenzyl bromideHCID 15812073HCID 15812073, Verbindung

Produkt 1

HCID 20064752HCID 20064752, VerbindungAusbeute 145,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A reaction vessel was charged with 100 ml of dimethylformamide, 6.11 g (50 mmol) of potassium carbonate, and 18 g (72 mmol) of o-bromobenzyl bromide. With this mixture stirred at ambient temperature under a nitrogen atmosphere, there was added 10 g (40 mmol) of 2-[(1,1-dimethylethyl)amino]-4-trifluoromethyl-5-oxazolecarboxylic acid (prepared by Example 26). The reaction mixture was stirred at ambient temperature for 18 hours. Then, the mixture was added to water and extracted three times with ethyl ether. The ether extracts were washed with large amounts of water, then dried over magnesium sulfate, and concentrated under reduced pressure to yield 24.5 g of a gold oil. This oil was subjected to Kugelrohr distillation (65°-70° C. @ 0.4 mm Hg) to yield 9.7 g of a gold oil. The remaining still residue upon standing at ambient temperature for 30 minutes formed a solid material. Trituration of this solid material in hexane at ambient temperature resulted in 11.48 g of a white solid product (m.p.=74°-77° C.) identified in Table I.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  2. extractionextracted three times with ethyl ether
  3. washThe ether extracts were washed with large amounts of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b321992e017a4974b8eab21d449202e5
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05000775

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