Alumina → HCID 18704059, compound

HRID 2288134Notes

Reaction equation

HRID 2288134 reaction equation
[O-2].[Al+3].[O-2].[O-2].[Al+3].[Cl:6][C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][C:10]2=[N:11][C:12](=[O:14])[N:13]=[C:9]2[CH:8]=1.[H][H]>N.O[V](=O)=O.[Pt].O>[NH2:17][C:16]1[C:7]([Cl:6])=[CH:8][C:9]2=[N:13][C:12](=[O:14])[N:11]=[C:10]2[CH:15]=1

Participants

7

Reactant 3

HCID 9989226AluminaHCID 18704057HCID 18704057, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18704059HCID 18704059, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 62684Ammonium metavanadate [UN2859] [Poison]CatalystHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

0.01 g of ammonium vanadate and 8 g of aluminium oxide granules containing 0.5% by weight of metallic platinum and having a particle size of 3.2 mm (from Acros Organics) are added to a suspension consisting of 200 ml of water and 21.4 g of 5-chloro-6-nitrobenzimidazolone. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at 65° C. At a hydrogen absorption of 85% of theory, another 50 ml of water are added to improve the stirrability and the mixture is then stirred at the same temperature under a hydrogen atmosphere for a total of 98 hours. During this time, 97% of the theoretical amount of hydrogen, based on 5-chloro-6-nitrobenzimidazolone, is absorbed. The resulting suspension is then sieved through a sieve having a mesh width of 1 mm. The material remaining on the sieve is washed with 50 ml of water and the combined aqueous phases are then filtered through a paper filter and washed with 100 ml of water. Drying at 80° C. under reduced pressure (125 mbar) gives 17.5 g (95%) of 5-amino-6-chlorobenzimidazolone. Only traces of 5-aminobenzimidazolone can be found in the NMR.

Workup

  1. additionare added to a suspension
  2. customAt a hydrogen absorption of 85% of theory
  3. additionanother 50 ml of water are added
  4. stirringthe mixture is then stirred at the same temperature under a hydrogen atmosphere for a total of 98 hours
  5. customis absorbed
  6. filtrationThe resulting suspension is then sieved through a sieve
  7. washis washed with 50 ml of water
  8. filtrationthe combined aqueous phases are then filtered through a paper
  9. filtrationfilter
  10. washwashed with 100 ml of water
  11. customDrying at 80° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record
ord-ced2c8162b23431e93508c2abd4aa544
Source dataset
uspto-grants-2000_07
Patent number
US06087480

Reaction notes

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