O-Phenylenediamine → HCID 12761781, compound

HRID 1155292Notes

Reaction equation

HRID 1155292 reaction equation
[ClH:1].[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[CH2:12][C:13](=[NH:17])OCC.[C:18]1(N)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24].[OH-].[NH4+]>C(O)C>[ClH:1].[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[CH2:12][C:13]1[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:24]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 14923Ammonium HydroxideHCID 12283309HCID 12283309, compound

Product 1

HCID 12761781HCID 12761781, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (1.4-benzodioxan-2-yl)acetimidate HCl, (5.0 g, 19.4 mmol) and o-phenylenediamine (2.16 g, 200 mmol) in ethanol (50 ml) were heated to reflux for 16 hours. The solution was cooled made basic with ammonium hydroxide, and extracted with ethyl acetate. The dried ethyl acetate extract was evaporated to a white solid which was triturated with ether and filtered to a white solid. This solid was dissolved in methanol and acidified with methanolic hydrogen chloride. The precipitated HCl salt was filtered and washed with ether to afford 2.4 g of 2-(1,4-benzodioxan-2-ylmethyl)benzimidazole hydrochloride, m.p. 230°-232°.

Workup

  1. temperatureto reflux for 16 hours
  2. temperatureThe solution was cooled
  3. extractionextracted with ethyl acetate
  4. extractionThe dried ethyl acetate extract
  5. customwas evaporated to a white solid which
  6. customwas triturated with ether
  7. filtrationfiltered to a white solid
  8. dissolutionThis solid was dissolved in methanol
  9. filtrationThe precipitated HCl salt was filtered
  10. washwashed with ether

Sources & evidence

ORD record
ord-6ebfeacfdc5a4fe3a2176b648841f00d
Source dataset
uspto-grants-1981_11
Patent number
US04301171

Reaction notes

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