Water → 2-[4-(Furan-2-yl)-1,3-thiazol-2-yl]-4,5,6,7-tetrahydro-1H-benzimidazole

HRID 2076921Notes

Reaction equation

HRID 2076921 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([C:11]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]2=O)=O)[S:9][CH:10]=1.FC(F)(F)C([O-])=O.[NH4+:28].O>C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([C:11]2[NH:28][C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=2)[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724268Ammonium trifluoroacetateHCID 671185394-(Furan-2-yl)-N-(2-oxocyclohexyl)-1,3-thiazole-2-carboxamide

Product 1

HCID 671186012-[4-(Furan-2-yl)-1,3-thiazol-2-yl]-4,5,6,7-tetrahydro-1H-benzimidazoleYield 28.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Furyl)-N-(2-oxocyclohexyl)thiazole-2-carboxamide (239 mg, 0.823 mmol) obtained in Step 2 and ammonium trifluoroacetate (1.00 g, 7.63 mmol) were stirred at 140° C. for 2 hours, and water and ethyl acetate were added thereto, then the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give a title compound (63.0 mg, 28%).

Workup

  1. extractionthe mixture was extracted
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fd55c7ea380a46ff9ecc7c27303eebca
Source dataset
uspto-grants-2011_04
Patent number
US07928098B2

Reaction notes

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