Ethyl isocyanate → N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 9177
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11]C#N)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15].[CH2:19]([N:21](CC)CC)C>CN(C)C=O>[CH3:11][C:9]1[CH:8]=[C:7]([C:19]#[N:21])[C:5]2[N:6]=[C:2]([NH:1][C:17]([NH:16][CH2:14][CH3:15])=[O:18])[S:3][C:4]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 21298164(2-Amino-1,3-benzothiazol-6-yl)acetonitrile

Produkt 1

HCID 21985550N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

About 1 g of (2-amino-1,3-benzothiazol-6-yl)methyl cyanide is dissolved in about 10 ml dimethylformamide. About 0.8 ml of ethylisocyanate is added followed by about 1.4 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4–6 hours then cooled to RT. The solvent is removed in vacuo and the solids are washed well with ether. The product is recrystallized from hot EtOAc. 1H NMR 1.09 (t, 3H), 3.1 (m, 2H), 4.1 (s, 2H), 6.72 (m, 1H), 7.32 (m, 1H), 7.61 (d, 1H), 7.85 (s, 1H), 10.7 (s, 1H); LC/MS 2.73 min, 261 (M+1), 259 (M−1).

Aufarbeitung

  1. temperaturethen cooled to RT
  2. customThe solvent is removed in vacuo
  3. washthe solids are washed well with ether
  4. customThe product is recrystallized from hot EtOAc
  5. customLC/MS 2.73 min, 261 (M+1), 259 (M−1)

Quellen und Nachweise

ORD-Eintrag
ord-157697f4a0e64340ac2d0e8d298b748a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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