Sodium Acetate → HCID 90229461, compound

HRID 1505780Notes

Reaction equation

HRID 1505780 reaction equation
Cl[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([N+:16]([O-:18])=[O:17])[CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:5]=2[N:4]=1.[C:19]([O-:22])(=[O:21])[CH3:20].[Na+]>CN(C=O)C>[C:19]([O:22][CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([N+:16]([O-:18])=[O:17])[CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:5]=2[N:4]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 90229430HCID 90229430, compound

Product 1

HCID 90229461HCID 90229461, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-(chloromethyl)-6-nitro-1H-benzimidazole-4-carboxylate (Example 58, Step 1) (99 mg) in DMF (1 mL), was added sodium acetate (17 mg), and the mixture was stirred at 50° C. for 6 hours. To the reaction mixture was added ice water, and it was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified on column chromatography to obtain the titled compound (65 mg) as colorless powder.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-fbdea4ac4b6e4533b859c4ff8aec9e41
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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