Dichloromethane → HCID 22380011, Verbindung

HRID 1594118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594118
Cl[CH2:2][C:3]1[N:4]([CH2:15][CH3:16])[C:5]2[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[CH2:15]([N:4]1[C:5]2[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1)[CH3:16]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 222603952-(1H-Imidazol-2-yl)-1,3-thiazoleHCID 223801501-(2-Chloromethyl-3-ethyl-3H-benzoimidazol-5-yl)-ethanone

Produkt 1

HCID 22380011HCID 22380011, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-Chloromethyl-3-ethyl-3H-benzoimidazol-5-yl)-ethanone (150 mg, 0.63 mmol), 2-(1H-Imidazol-2-yl)-thiazole (95 mg, 0.63 mmol) and K2CO3 (262 mg, 1.9 mmol)in DMF (10 mL) is stirred at room temperature for 48 hours. Brine (6 mL) and DCM (20 mL) are added. The organic layer is separated and the aqueous layer is extracted with DCM (3×29 mL). The combined organic layers are dried and solvent removed. The residue is purified by PTLC (10% methanol in DCM) to give 1-[3-Ethyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-3H-benzoimidazol-5-yl]-ethanone as a solid. 1H NMR (CDCl3) δ 8.05 (d, 1H), 7.92 (dd, 1H), 7.87 (dd, 1H), 7.81 (dd, 1H), 7.40 (d, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 6.17 (s, 2H), 4.33 (q, 2H), 2.67 (s, 3H), 1.13 (t, 3H).

Aufarbeitung

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with DCM (3×29 mL)
  3. customThe combined organic layers are dried
  4. customsolvent removed
  5. customThe residue is purified by PTLC (10% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8f86279a12f84807914d5ef87fb19a2d
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300945B2

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