2-Aminophenol → HCID 86664947, compound

HRID 74152Notes

Reaction equation

HRID 74152 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1O.C(N(CC)CC)C.CCN=C=NCCCN(C)C.[CH3:40][S:41]([OH:44])(=[O:43])=[O:42]>O1CCOCC1.O.C(Cl)(Cl)Cl>[CH3:40][S:41]([OH:44])(=[O:43])=[O:42].[O:13]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:11]1[C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[NH:3][C:4]=2[CH:10]=1

Participants

9

Reactant 5

HCID 58012-AminophenolHCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11326092-methyl-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 86664947HCID 86664947, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Methylbenzimidazole-5-carboxylic acid (1.00 g, 5.7 mmol), 2-aminophenol (0.68 g, 6.2 mmol), chloroform (20 mL), triethylamine (0.69 g, 6.8 mmol), and WSC (1.20 g, 6.2 mmol) were stirred overnight at room temperature. After the reaction was complete, water (50 mL) was added to the residue from concentration, and this was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, filtration and concentration gave crystals that were dissolved in dioxane (30 mL), to which methanesulfonic acid (0.48 mL) was added and this was stirred at reflux for 10 hours. After cooling a precipitated solid was filtered off, and washing with THF and drying under reduced pressure at 50° C. yielded the title compound (0.82 g, 42% yield) as a white solid.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, filtration and concentration
  3. customgave crystals that
  4. additionwas added
  5. temperatureat reflux for 10 hours
  6. temperatureAfter cooling a precipitated solid
  7. filtrationwas filtered off
  8. washwashing with THF
  9. customdrying under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-48e0f686d39c4f65b24937145b545d10
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

Loading…