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Acetonitrile → methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate

HRID 1189452
Notes
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Reaction equation

HRID 1189452 reaction equation
F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.FC1C=CC(C(OC)=O)=C(C)C=1[N+]([O-])=O.[CH:31]1([C:36]2[NH:37][CH:38]=[CH:39][N:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1.C(#N)C>C(OCC)(=O)C.O.C(N(CC)CC)C>[CH:31]1([C:36]2[N:37]([C:2]3[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=3)[CH:38]=[CH:39][N:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 150886132-Cyclopentyl-1H-imidazoleHCID 51342041Methyl 4-fluoro-2-methyl-5-nitrobenzoateHCID 58575232Methyl 4-fluoro-2-methyl-3-nitrobenzoate

Product 1

HCID 58575136methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8471TriethylamineSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 2.74 g of a mixture of methyl 4-fluoro-2-methyl-5-nitrobenzoate and methyl 4-fluoro-2-methyl-3-nitrobenzoate, 1.75 g of 2-cyclopentyl-1H-imidazole, and 17.5 mL of acetonitrile, was added 4.9 mL of triethylamine, followed by stirring at 70° C. for 7 hours. To the reaction mixture were added water and ethyl acetate, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and then solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 2.12 g of methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customsolvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3e1235f3dad24a468de08e7ea9b791e2
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08674096B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes