HCID 66636876, compound → HCID 86629736, compound

HRID 551061Notes

Reaction equation

HRID 551061 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:7](=[O:14])[N:8]([CH2:9][C:10](OC)=[O:11])[C:4]=2[C:3]=1[N+:22]([O-])=O>CC(O)=O.O.[Fe]>[Cl:1][C:2]1[C:3]2[NH:22][C:10](=[O:11])[CH2:9][N:8]3[C:7](=[O:14])[N:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:5]([C:4]=23)=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 66636876HCID 66636876, compound

Product 1

HCID 86629736HCID 86629736, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of dimethyl 2,2′-(5-chloro-4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate (100 mg, 0.28 mmol) from Step D in AcOH (1.0 mL) and water (0.1 mL) was added fine granular iron (78 mg, 1.4 mmol) and the slurry was heated at 70° C. for 1 h. The reaction was cooled, filtered, concentrated and dissolved in DMF (4 mL). The DMF solution was added dropwise to H2O (30 mL) with stirring and the precipitate was isolated by filtration to give the title compound. MS: m/z=296 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutiondissolved in DMF (4 mL)
  5. additionThe DMF solution was added dropwise to H2O (30 mL)
  6. customthe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-242afe27c63b4ef88678ddf76ae6647b
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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