Allyl Isothiocyanate → 2-(2,6-dichlorophenylamino)-3-methyl-5-(3-allyl-thioureido)-3H-benzimidazole-4-carboxylic acid amide

HRID 1760754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760754
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:10][C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:8]([CH3:9])[C:4]=2[C:3]=1[C:21]([NH2:23])=[O:22].[CH2:24]([N:27]=[C:28]=[S:29])[CH:25]=[CH2:26]>CN(C=O)C.[Cl-].[Na+].O>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[NH:10][C:7]1[N:8]([CH3:9])[C:4]2[C:3]([C:21]([NH2:23])=[O:22])=[C:2]([NH:1][C:28]([NH:27][CH2:24][CH:25]=[CH2:26])=[S:29])[CH:20]=[CH:19][C:5]=2[N:6]=1

Komponenten

5

Edukt 2

HCID 5971Allyl IsothiocyanateHCID 113939665-Amino-2-(2,6-dichlorophenylamino)-3-methyl-3H-benzoimidazole-4-carboxylic acid amide

Produkt 1

HCID 229015642-(2,6-dichlorophenylamino)-3-methyl-5-(3-allyl-thioureido)-3H-benzimidazole-4-carboxylic acid amideAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of 100 mg (0.286 mmol) of 5-amino-2-(2,6-dichlorophenylamino)-3-methyl-3H-benzimidazole-4-carboxylic acid amide (Example 7) and 114 mg (1.15 mmol) of allyl isothiocyanate in DMF was warmed at 45° C. for 48 h. The reaction was diluted with 30 mL of brine and extracted with four 15 mL portions of EtOAc. The combined organic layers were washed with five 15 mL portions of brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel (MeOH-methylene chloride, first 2:98, then 4:96, then 5:95) to afford 66 mg (51%) of 2-(2,6-dichlorophenylamino)-3-methyl-5-(3-allyl-thioureido)-3H-benzimidazole-4-carboxylic acid amide.

Aufarbeitung

  1. extractionextracted with four 15 mL portions of EtOAc
  2. washThe combined organic layers were washed with five 15 mL portions of brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (MeOH-methylene chloride, first 2:98

Quellen und Nachweise

ORD-Eintrag
ord-40928cb410b74d1699a3102d004008a5
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844435B2

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