Water → HCID 68138675, compound

HRID 268241

Reaction equation

HRID 268241 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-])=O.O.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.S([O-])([O-])(=O)=O.[Ca+2]>C(O)C.[Pd].CC(O)=O>[N:8]1[C:7]2[CH:11]=[CH:12][C:4]([NH:1]/[C:16](/[CH3:18])=[CH:15]\[C:14]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][C:6]=2[NH:10][CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 71955-NitrobenzimidazoleHCID 8868Ethyl AcetoacetateHCID 24497Calcium Sulfate

Product 1

HCID 68138675HCID 68138675, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

An 82 g. (0.5 mole) sample of 5-nitrobenzimidazole in 900 ml of ethanol was reduced over 4 g. of 5% Pd/C catalyst containing 50% H2O. After a pressure drop of 108 lb. (calcd. 106 lb.), the reduction stopped. After filtration of the catalyst, 65 g. (0.5 mole) of ethyl acetoacetate, 20 g. of anhydrous calcium sulfate, and 0.5 ml of HOAc was added. After filtration of the anhydrous calcium sulfate the solution was concentrated in vacuo till till a solid remained. The product was filtered and washed with fresh ethanol and air-dried. The yield was 84 g. (69%), m.p. 160°-162°C.

Workup

  1. filtrationAfter filtration of the catalyst, 65 g
  2. filtrationAfter filtration of the anhydrous calcium sulfate the solution
  3. concentrationwas concentrated in vacuo till till a solid
  4. filtrationThe product was filtered
  5. washwashed with fresh ethanol
  6. customair-dried

Sources & evidence

ORD record
ord-9aee42b105fd42508b68c12497ef38d1
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Linked notes

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