2-Aminothiazole → 1,1-Dicyclohexyl-3-thiazol-2-yl-urea

HRID 2384129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384129
[CH:1]1[N:5]=[C:4]([NH2:6])[S:3][CH:2]=1.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].[CH:19]1([NH:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl.C(OCC)(=O)C>[CH:26]1([N:25]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:7]([NH:6][C:4]2[S:3][CH:2]=[CH:1][N:5]=2)=[O:8])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Komponenten

6

Edukt 3

HCID 21552-AminothiazoleHCID 7582DicyclohexylamineHCID 682631,1'-Carbonyldiimidazole

Produkt 1

HCID 111742841,1-Dicyclohexyl-3-thiazol-2-yl-urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of aminothiazole (50 mg, 0.5 mmol) in dichloromethane was added carbonyldiimidazole (81 mg, 0.5 mmol) and the solution stirred 2 h at room temperature. Dicyclohexylamine (1 eq) was then added and the reaction stirred overnight at room temperature. The reaction mixture is then diluted with ethyl acetate (8 mL), washed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL), dried over magnesium sulphate, concentrated in vacuo, and the residue purified by HPLC (Gilson 1, X-terra column; 0-100% CH3CN/H2O/0, 1% TFA; 15 min; flow 50 ml/min) to give the title product (52 mg).

Aufarbeitung

  1. stirringthe reaction stirred overnight at room temperature
  2. washwashed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by HPLC (Gilson 1, X-terra column; 0-100% CH3CN/H2O/0, 1% TFA; 15 min; flow 50 ml/min)

Quellen und Nachweise

ORD-Eintrag
ord-acbbe392b1d0489591f06f537dd8fdbe
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263634B2

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