Formic Acid → HCID 54472847, compound

HRID 866254Notes

Reaction equation

HRID 866254 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:47]=[CH:46][C:12]2[N:13]([CH:16]([C:22]3[N:23](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:24]=[CH:25][N:26]=3)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[N:15][C:11]=2[CH:10]=1)#[N:2].C(O)=O.[H-].[Na+].Br[CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56]>CCOCC.O.CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:47]=[CH:46][C:12]2[N:13]([CH:16]([C:22]3[N:23]([CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:24]=[CH:25][N:26]=3)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[N:15][C:11]=2[CH:10]=1)#[N:2]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 21468916HCID 21468916, compound

Product 1

HCID 54472847HCID 54472847, compoundYield 0.1%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

2-[1-[5-(2-Cyanophenyl)-1H-benzimidazol-1-yl]hexyl]-1-trityl-1H-imidazole (3.44 moles, 2.1 g) was dissolved in 200 ml ether, 240 ml formic acid, and 24 drops of water. The solution was stirred for 1 hour at room temperature and concentrated. Ethyl acetate was added. The ethyl acetate solution was washed with water, dried over sodium sulfate, filtered and concentrated. The residue was dissolved in 50 ml DMF. Sodium hydride (3.8 mmoles, 152 mg of 60% in mineral oil) was added. The reaction was stirred at room temperature for 2 hours. Ethyl bromoacetate (3.8 moles, 0.634 g.) in 50 ml DMF was added. The reaction was stirred for 1 hour, poured into ice water, and extracted with ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate, and concentrated. The intermediate was purified by chromatography over silica gel eluted with ethyl acetate to give 830 mg of ethyl 2-[1-[5-(2-cyanophenyl)1H-benzimidazol-1-yl]hexyl]-1H-imidazole-1-acetate. (MS)

Workup

  1. concentrationconcentrated
  2. additionEthyl acetate was added
  3. washThe ethyl acetate solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 50 ml DMF
  8. stirringThe reaction was stirred at room temperature for 2 hours
  9. stirringThe reaction was stirred for 1 hour
  10. extractionextracted with ethyl acetate
  11. washThe organic solution was washed with brine
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated
  14. customThe intermediate was purified by chromatography over silica gel
  15. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-b71d8c124cf94e68836cc3c1bf4b1858
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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