Water → HCID 178470543, compound

HRID 986820Notes

Reaction equation

HRID 986820 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.[OH2:13].C([O:16][C:17](=[C:21]([C:25]([O-])=O)C([O-])=O)[O:18][CH2:19][CH3:20])C.[CH:28]1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>C(O)C.[Pd]>[OH:13][C:21]1([C:17]([O:18][CH2:19][CH3:20])=[O:16])[C:5]2[C:4]([CH:12]=[CH:11][C:7]3[C:6]=2[NH:10][CH2:9][N:8]=3)=[N:1][CH:28]=[CH:25]1

Participants

7

Reactant 4

HCID 962Water2×HCID 71955-NitrobenzimidazoleHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 23435867Diethoxymethylenemalonate

Product 1

HCID 178470543HCID 178470543, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

An 82 g. portion (0.5 mole) of 5-nitrobenzimidazole in 1 L of ethanol is reduced over 5 g. of 5% palladium-charcoal catalyst containing 50% water. The reduction stops after a pressure drop of 97 psig. (97%) in 75 min. The catalyst is filtered, 108 g. (0.5 mole) of diethoxymethylenemalonate is added to the filtrate and the solution is boiled in an open flask until about one-half of the solvent has boiled away (ca. 2 hr.). The product sets to a solid cake upon cooling. Ethanol containing a little water is added to assist in breaking up the cake and the product is filtered, washed with cold ethanol-H2O (3:1) and air-dried; yield, 125 g. (83%). A 50 g. portion of this anil is added to 500 ml. of boiling Dowtherm over a 3-4 min. period and boiling is continued 4 min. longer. After cooling to room temperature the product is filtered, washed with Dowtherm, then benzene and air-dried; 44 g. of crude product is obtained. Extraction of this material with 500 ml. of boiling ethanol gives 22 g., m.p. 315°-316° C.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solution is boiled in an open flask until about one-half of the solvent
  3. custom(ca. 2 hr.)
  4. temperatureupon cooling
  5. filtrationthe product is filtered
  6. washwashed with cold ethanol-H2O (3:1)
  7. customair-dried
  8. customyield
  9. additionportion of this anil is added to 500 ml
  10. filtrationis filtered
  11. washwashed with Dowtherm
  12. dry with materialbenzene and air-dried
  13. customof crude product is obtained
  14. extractionExtraction of this material with 500 ml
  15. customof boiling ethanol gives 22 g

Sources & evidence

ORD record
ord-560b8435c78d49978cbae6b6b886ee53
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Reaction notes

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