HCID 66636876, compound → HCID 86629736, compound

HRID 2353286Notes

Reaction equation

HRID 2353286 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-d5537346b1e0448a83310dfddcd2f596
Source dataset
uspto-grants-2010_07
Patent number
US07750010B2

Reaction notes

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