O-Phenylenediamine → 2-[(3-methoxyphenoxy)methyl]-1H-benzimidazole

HRID 537297Notes

Reaction equation

HRID 537297 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[O:14][CH2:15][C:16](O)=O>Cl>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:16]=1[CH2:15][O:14][C:13]1[CH:19]=[CH:20][CH:21]=[C:11]([O:10][CH3:9])[CH:12]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 749692-(3-Methoxyphenoxy)acetic acid

Product 1

HCID 10854502-[(3-methoxyphenoxy)methyl]-1H-benzimidazoleYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of phenylenediamine (15.12 g, 0.14 mol) and 3-methoxyphenoxyacetic acid (25.5 g, 0.14 mol) in 4M HCl (150 mL) was refluxed overnight under Ar. The reaction mixture was cooled in an ice bath. The solid was collected and washed with cold H2O (200 mL). To the solid was added CH2Cl2 (150 mL) and saturated NaHCO3 (150 mL). After stirring for 1 hr, the organic phase was separated, washed with brine (75 mL), filtered through phase separation filter paper and concentrated in vacuo to give 32.7 g (92%) of 51 as an oil which solidified. The HPLC analysis showed a purity of 98%. 1H NMR (60 MHz, CDCl3): δ 10.0 (br s, 1H), 6.3-7.9 (m, 8H), 5.0 (s, 2H), 3.7 (s, 3H) ppm.

Workup

  1. temperaturewas refluxed overnight under Ar
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customThe solid was collected
  4. washwashed with cold H2O (200 mL)
  5. additionTo the solid was added CH2Cl2 (150 mL) and saturated NaHCO3 (150 mL)
  6. customthe organic phase was separated
  7. washwashed with brine (75 mL)
  8. filtrationfiltered through phase separation
  9. filtrationfilter paper
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d26a63a133c04cf8bf829872b340e09f
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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