Morpholine → 2-(morpholin-4-yl)-4-nitro-1H-benzimidazole

HRID 2298812Notes

Reaction equation

HRID 2298812 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.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])O.[Na+]>>[N:14]1([C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=3[N:3]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 14765451HCID 14765451, compound

Product 1

HCID 183786202-(morpholin-4-yl)-4-nitro-1H-benzimidazole

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-4-nitro-1H-benzimidazole (300 mg) and morpholine (1 ml) was stirred at 50° C. for 8 hours. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo. The residue was washed with isopropyl ether and collected by vacuum filtration to give 2-(morpholin-4-yl)-4-nitro-1H-benzimidazole (288 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. washThe residue was washed with isopropyl ether
  6. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-1974a1f013ee4591b081c81e72c586ad
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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