Ethanol → HCID 53666222, compound

HRID 986819Notes

Reaction equation

HRID 986819 reaction equation
C(O)C.[N+:4]([C:7]1[CH:15]=[CH:14][C:10]2[N:11]=[CH:12][NH:13][C:9]=2[CH:8]=1)([O-])=O.[CH2:16]([O:18][C:19](=[O:29])[CH2:20][C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:17].S([O-])([O-])(=O)=O.[Ca+2]>O.CC(O)=O>[N:11]1[C:10]2[CH:14]=[CH:15][C:7]([NH:4][C:24]3[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=3)[CH:21]=[CH:20][C:19]([O:18][CH2:16][CH3:17])=[O:29])=[CH:8][C:9]=2[NH:13][CH:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 7170Ethyl benzoylacetateHCID 71955-NitrobenzimidazoleHCID 24497Calcium Sulfate

Product 1

HCID 53666222HCID 53666222, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 900 ml. of ethanol and 82 g. (0.5 mole) of 5-nitrobenzimidazole with 4 g. of 5% PdC, 50% H2O catalyst is reduced on the Parr Apparatus. A pressure drop of 104 psi. is observed (calcd. 100). After the reduction stopped, the bottle is removed from the apparatus, and the catalyst filtered. Then 96 g. (0.5 mole) of ethylbenzoylacetate, 20 g. of anhydrous calcium sulfate and 0.5 ml. of HOAc are added to the filtrate. The solution is refluxed for 2 hours and filtered. The filtrate is concentrated to a dark sticky resin. Crystallization is induced by scratching. The product after cooling is filtered, washed with ethanol and air-dried. The product weighs 55 g. m.p. 188°-190° C.

Workup

  1. customthe bottle is removed from the apparatus
  2. filtrationthe catalyst filtered
  3. temperatureThe solution is refluxed for 2 hours
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated to a dark sticky resin
  6. customCrystallization
  7. temperatureThe product after cooling
  8. filtrationis filtered
  9. washwashed with ethanol
  10. customair-dried

Sources & evidence

ORD record
ord-c6cf0654a63b4e1a832a8429571efb32
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Reaction notes

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