O-Phenylenediamine → HCID 21459115, compound

HRID 274544Notes

Reaction equation

HRID 274544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([OH:20])[C:15](=[NH:19])OCC)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10].[C:21]1(N)[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:27]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([C:15]2[NH:19][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:27]=2)[OH:20])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 19000171HCID 19000171, compound

Product 1

HCID 21459115HCID 21459115, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

19.7 g of ethyl (3,4-dimethoxy-5-nitro-phenyl)hydroxyacetimidate are dissolved in 500 ml of ethanol, 6.73 g of o-phenylenediamine are added, the mixture is stirred at room temperature for 2 hours and subsequently held at the reflux temperature overnight. After distillation of the solvent, the residue is treated with 50 ml of water, made alkaline with sodium carbonate solution and extracted twice with 250 ml of methylene chloride each time. The organic phase is washed with water, dried over sodium sulfate and evaporated. The orange residue obtained is chromatographed on 400 g of silica gel with methylene chloride/ethyl acetate (1:1). From ether/hexane there is obtained α-(3,4-dimethoxy-5-nitrophenyl)-2-benzimidazolemethanol in the form of yellowish crystals of m.p. 50° (dec.).

Workup

  1. customsubsequently held at the reflux temperature overnight
  2. distillationAfter distillation of the solvent
  3. additionthe residue is treated with 50 ml of water
  4. extractionextracted twice with 250 ml of methylene chloride each time
  5. washThe organic phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe orange residue obtained
  9. customis chromatographed on 400 g of silica gel with methylene chloride/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-88395fef0d79463db66e1d24a839c336
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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