1-Amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromide → HCID 178485720, Verbindung

HRID 482263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482263
O(C)[Na].CO.Br.[C:7]([N:10]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]1=[O:17])(=[NH:9])[NH2:8].[CH3:18][N:19]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)[C:20](=[O:28])[C:21]([C:26]#[N:27])=[CH:22]OCC>CO>[C:26]([C:21]([C:20](=[O:28])[N:19]([CH3:18])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)=[CH:22][NH:9][C:7](=[NH:8])[N:10]1[CH2:14][C:13]([CH3:15])([CH3:16])[NH:12][C:11]1=[O:17])#[N:27]

Komponenten

5

Edukt 3

HCID 190638771-Amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromideHCID 536402872-cyano-3-ethoxyacrylic acid N-methyl-N-(3-trifluoromethylphenyl)amideHCID 178501943HCID 178501943, Verbindung

Produkt 1

HCID 178485720HCID 178485720, VerbindungAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

3.60 g (=3.67 ml, 20 mmol) of 30% strength NaOCH3 /CH3OH solution were added to a solution of 4.74 g (20 mmol) of 1-amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromide in 47 ml of methanol at room temperature, and the mixture was stirred at 45° C. for 30 min. The solution was then cooled to 20° C. and, at 20° C., 5.97 g (20 mmol) of 2-cyano-3-ethoxyacrylic acid N-methyl-N-(3-trifluoromethylphenyl)amide were added and the mixture was stirred at 20° C. for 20 min, at room temperature for 1.5 hours and while cooling in an icebath for 30 min. The solid which had separated out was filtered off with suction, washed with ether and worked up further as described in Example 1. Likewise, the residue from the filtrate (mother liquor) was further worked up as described in Example 1 and dried. 6.35 g (=77.7% yield) of, according to TLC (CH2Cl2 /C2H5 OH=10:1), virtually pure compound IV were obtained.

Aufarbeitung

  1. temperatureThe solution was then cooled to 20° C. and, at 20° C.
  2. stirringthe mixture was stirred at 20° C. for 20 min, at room temperature for 1.5 hours
  3. temperaturewhile cooling in an icebath for 30 min
  4. customThe solid which had separated out
  5. filtrationwas filtered off with suction
  6. washwashed with ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5a9461b0445d45339dfc96697416e4b4
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795899

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