Dimethylformamide → 3-(2-Cyano-acetyl)-3-methyl-1-(2-isocyanobenzyl)-urea

HRID 78687

Reaktionsgleichung

Reaktionsgleichung von HRID 78687
[N+:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[CH2:5][NH:6][C:7]([NH:9][CH3:10])=[O:8])#[C-:2].[C:15]([CH2:17][C:18]([OH:20])=O)#[N:16].CN(C)C=O.CS(Cl)(=O)=O>O.C(O)(C)C.O>[C:15]([CH2:17][C:18]([N:9]([CH3:10])[C:7](=[O:8])[NH:6][CH2:5][C:4]1[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=1[N+:1]#[C-:2])=[O:20])#[N:16]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 31297Methanesulfonyl chlorideHCID 580761271-(2-Isocyanobenzyl)-3-methylurea

Produkt 1

HCID 580761243-(2-Cyano-acetyl)-3-methyl-1-(2-isocyanobenzyl)-ureaAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21889133Propan-2-ol--water (1/1)Lösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, 1-(2-isocyanobenzyl)-3-methylurea (98.4 g) and cyanoacetic acid (80.0 g) was added to N,N-dimethylformamide (836 ml). The mixture was stirred at room temperature and methanesulfonyl chloride (72.8 ml) was added dropwise with stirring at this temperature. The mixture was stirred at room temperature for 4 hrs, cooled with water, and water-isopropanol [2:1 (volume ratio), 1670 ml] was added drop wise. The mixture was stirred under water-cooling for 1 hr, and the precipitated crystals were collected by filtration and dried to give 3-(2-cyano-acetyl)-3-methyl-1-(2-isocyanobenzyl)-urea with 68% yield.

Aufarbeitung

  1. stirringwith stirring at this temperature
  2. stirringThe mixture was stirred at room temperature for 4 hrs
  3. additionwas added drop wise
  4. stirringThe mixture was stirred under water-
  5. temperaturecooling for 1 hr
  6. filtrationthe precipitated crystals were collected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2d62973b998f4ada92c1a893133f91ed
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841447B2

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