Ethanol hydrochloride → HCID 90229258, compound

HRID 1505805Notes

Reaction equation

HRID 1505805 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([N:20]([CH3:22])[CH3:21])[NH:16][C:15]=3[CH:14]=[C:13]([N+:23]([O-])=O)[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.CCO>CO.C1COCC1.[Pt]>[NH2:23][C:13]1[CH:12]=[C:11]([C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[CH3:26])=[O:10])[C:19]2[N:18]=[C:17]([N:20]([CH3:21])[CH3:22])[NH:16][C:15]=2[CH:14]=1

Participants

5

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 90229388HCID 90229388, compound

Product 1

HCID 90229258HCID 90229258, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of N-(3-chloro-2-methylphenyl)-2-(dimethylamino)-6-nitro-1H-benzimidazole-4-carboxamide (580 mg) in MeOH-THF (1:1, 60 mL), was added 2N hydrogen chloride/EtOH (1 mL). To the mixture was added 1% platinum+0.1% copper-activated carbon (Degussa type CF105 R/W) (150 mg) and it was stirred vigorously under hydrogen atmosphere (0.2 MPa) for 3 hours. The reaction mixture was filtered off through celite, and the mother liquid was concentrated. To the residue was added saturated aqueous sodium bicarbonate, and it was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (265 mg) as brown powder.

Workup

  1. filtrationThe reaction mixture was filtered off through celite
  2. concentrationthe mother liquid was concentrated
  3. additionTo the residue was added saturated aqueous sodium bicarbonate, and it
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-953df31972b14ffe89403cb1cb5d18d6
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

Loading…