HCID 67293292, compound → HCID 59276512, compound

HRID 2070866Notes

Reaction equation

HRID 2070866 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:7]2[CH:19]=[CH:20][C:21](N)=[CH:22][C:6]=2[N:5]=1.COCC1N(S(C2C=CC(C)=CC=2)(=O)=O)C2C=CC([N+]([O-])=O)=CC=2[N:28]=1>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[N:8]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=2)(=[O:11])=[O:10])[C:7]2[CH:19]=[C:20]([NH2:28])[CH:21]=[CH:22][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 67293292HCID 67293292, compoundHCID 68588158HCID 68588158, compound

Product 1

HCID 59276512HCID 59276512, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Methoxymethyl)-1-tosyl-1H-benzo[d]imidazol-5-amine. 2-(Methoxymethyl)-5-nitro-1-tosyl-1H-benzo[d]imidazole (0.9 g, 2.491 mmol) were dissolved in ethanol and purged with nitrogen. Palladium on activated carbon was added (0.530 g, 0.498 mmol), the nitrogen was evacuated and the reaction was stirred under 1 atmosphere of hydrogen for 16 h. The reaction mixture was filtrated through Celite and washed with ethanol. The organic layer was concentrated on a rotary evaporator to dryness to give desired product as purple solid, which was then crystallized from ethyl acetate in hexane to give the desired compound as a white solid (0.7 g, 85% yield). MS (ESI) m/z 332.2 [M+1]+.

Workup

  1. custompurged with nitrogen
  2. additionPalladium on activated carbon was added (0.530 g, 0.498 mmol)
  3. customthe nitrogen was evacuated
  4. filtrationThe reaction mixture was filtrated through Celite
  5. washwashed with ethanol
  6. concentrationThe organic layer was concentrated on a rotary evaporator to dryness

Sources & evidence

ORD record
ord-5a96afa3f6bf494fad46d2c8a996cbba
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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