Sodium Hydroxide → 2-(2-methoxyethyl)-4-methyl-1H-benzo[d]imidazol-6-ol

HRID 1846506Notes

Reaction equation

HRID 1846506 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH3:9])[C:7]=1[NH2:8].[CH3:11][O:12][CH2:13][CH2:14][C:15](O)=O.[OH-].[Na+]>CO>[CH3:11][O:12][CH2:13][CH2:14][C:15]1[NH:1][C:2]2[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH3:9])[C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1344423-Methoxypropionic acidHCID 199076443,4-Diamino-5-methylphenol

Product 1

HCID 669783192-(2-methoxyethyl)-4-methyl-1H-benzo[d]imidazol-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

0.65 g (4.70 mmol) 3,4-diamino-5-methylphenol were placed in a little methanol and 0.94 mL (10.00 mmol) 3-methoxypropionic acid was added. First the methanol was distilled off and then the mixture was stirred for 2 h at 140° C. The reaction mixture was taken up in DMF/MeOH and purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous 4M NaOH solution and extracted with ethyl acetate. The organic phase was dried and evaporated down i.vac. and dried.

Workup

  1. additionwas added
  2. distillationFirst the methanol was distilled off
  3. custompurified by chromatography
  4. additionThe fractions containing product
  5. customevaporated down i.vac
  6. customto leave the aqueous residue
  7. extractionextracted with ethyl acetate
  8. customThe organic phase was dried
  9. customevaporated down i.vac
  10. customand dried

Sources & evidence

ORD record
ord-c6682442a1384ae3846132a6c997a4c5
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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