5-Nitro-2H-benzimidazol-2-one → 5-amino-2H-1,3-benzodiazol-2-one

HRID 2288132Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2=[N:8][C:9](=[O:11])[N:10]=[C:6]2[CH:5]=1)([O-])=O.[H][H]>N.O[V](=O)=O.[O-2].[O-2].[Ti+4].[Pd].O>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]2=[N:8][C:9](=[O:11])[N:10]=[C:6]2[CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.001 g of ammonium vanadate and 0.5 g of titanium dioxide extrudate containing 1% by weight of metallic palladium and having a particle size of 3 mm (from Johnson Matthey) are added to a suspension consisting of 50 ml of water and 1.8 g of 5-nitrobenzimidazolone. After displacing the air with nitrogen, the latter is replaced by hydrogen at atmospheric pressure and the suspension is stirred at 60° C. for 34 hours. During this time, 102% of the theoretical amount of hydrogen, based on the 5-nitrobenzimidazolone, is adsorbed. 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 250 ml of water. Drying at 80° C. under reduced pressure (125 mbar) gives 1.2 g (79%) of 5-aminobenzimidazolone.

Workup

additionare added to a suspension
filtrationThe resulting suspension is then sieved through a sieve
washis washed with 50 ml of water
filtrationthe combined aqueous phases are then filtered through a paper
filtrationfilter
washwashed with 250 ml of water
customDrying at 80° C. under reduced pressure (125 mbar)

Sources & evidence

ORD record: ord-9ec8319f60e4407f9137c5b4e3491b44
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087480

Reaction notes

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