Ethyl Acetate → HCID 18681095, compound

HRID 276073Notes

Reaction equation

HRID 276073 reaction equation
[C:1]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[NH2:17])(=O)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:24][C:25]1[CH:40]=[CH:39][C:28]([CH2:29][O:30][C:31]2[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=2)=[CH:27][CH:26]=1.C(OCC)(=O)C>O>[CH2:13]([O:12][C:10]([C:9]1[CH:15]=[CH:16][C:6]2[N:5]=[C:1]([CH2:2][CH3:3])[N:17]([CH2:35][C:34]3[CH:37]=[CH:38][C:31]([O:30][CH2:29][C:28]4[CH:39]=[CH:40][C:25]([F:24])=[CH:26][CH:27]=4)=[CH:32][CH:33]=3)[C:7]=2[CH:8]=1)=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18315520HCID 18315520, compoundHCID 18680960HCID 18680960, compound

Product 1

HCID 18681095HCID 18681095, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 0.534 g of ethyl 4-propionylamino-3-aminobenzoate, 0.374 g of potassium carbonate, 0.800 g of 4-(4-fluorobenzyloxy)benzyl bromide, 5 ml of ethyl acetate and 3 ml of water was stirred at 75° C. for 16 hours. The organic layer was concentrated, and ethanol and 0.46 g of 36% hydrochloric acid were added to the residue. The mixture was stirred for 2 hours while being heat-refluxed. The reaction mixture was neutralized with potassium carbonate, and the solvent was then concentrated under reduced pressure. The residue was extracted with ethyl acetate and with water. The organic layer was concentrated under reduced pressure, and was purified through silica-gel column chromatography (eluent: a mixture of hexane and ethyl acetate at a ratio of 1:1) to give 0.228 g of 6-ethoxycarbonyl-2-ethyl-1-[4-(4-fluorobenzyloxy)benzyl]benzimidazole (325).

Workup

  1. concentrationThe organic layer was concentrated
  2. additionethanol and 0.46 g of 36% hydrochloric acid were added to the residue
  3. stirringThe mixture was stirred for 2 hours
  4. temperaturewhile being heat-refluxed
  5. concentrationthe solvent was then concentrated under reduced pressure
  6. extractionThe residue was extracted with ethyl acetate and with water
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customwas purified through silica-gel column chromatography (eluent
  9. additiona mixture of hexane and ethyl acetate at a ratio of 1:1)

Sources & evidence

ORD record
ord-a8200f158a064d7ea64dc9cac153f2b4
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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