Sodium Carbonate → HCID 66976923, compound

HRID 44484Notes

Reaction equation

HRID 44484 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:20]=[C:21]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:22]=[C:23]([N+:24]([O-])=O)[C:6]=2[N:5]=1)[CH3:3].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:3][CH:2]([C:4]1[N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:20]=[C:21]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[CH:22]=[C:23]([NH2:24])[C:6]=2[N:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 669769602-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole

Product 1

HCID 66976923HCID 66976923, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

TiCl3 (16.3 mL) was added to a solution of 2-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole (1.6 g) and NH4OAc (4 g) in MeOH (40 mL). After stirring for 4 h at room temperature, TLC showed no starting material. The pH of the mixture was made basic by adding Na2CO3 aqueous solution. The solvent was evaporated off under reduced pressure and the residue was extracted with DCM (250 mL×2). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in-vacuo to afford the desired product as a white solid (1.2 g, 81%). LC-MS: m/e=401 [M+1]+.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. extractionthe residue was extracted with DCM (250 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-d1b8a5b4b7c24dd1a1d57cc2b58f961e
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Reaction notes

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