N,N-Dimethylethylenediamine → 2-[2-(dimethylamino)ethylamino]-4-nitro-1H-benzimidazole

HRID 429653Notes

Reaction equation

HRID 429653 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=2[N:3]=1.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18].C(=O)(O)[O-].[Na+]>>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:18][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 14765451HCID 14765451, compound

Product 1

HCID 183786772-[2-(dimethylamino)ethylamino]-4-nitro-1H-benzimidazole

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-4-nitro-1H-benzimidazole (300 mg) and N,N-dimethylethylenediamine (2 ml) were stirred at 80° C. for 8 hours. The reaction mixture was poured into saturated sodium bicarbonate aqueous solution and extracted with a mixture of chloroform and methanol. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The resiude was washed with diisopropyl ether to give 2-[[2-(dimethylamino)ethyl]amino]-4-nitro-1H-benzimidazole (113 mg).

Workup

  1. extractionextracted with a mixture of chloroform and methanol
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe resiude was washed with diisopropyl ether

Sources & evidence

ORD record
ord-717ff083e89c4fddb7799ab63eab60f0
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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