2-Aminophenol → HCID 15661967, compound

HRID 1081894Notes

Reaction equation

HRID 1081894 reaction equation
S(Cl)(Cl)=O.[CH2:5]([C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:6][CH2:7][CH3:8].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1O.[OH-].[Na+]>CN1CCCC1=O>[CH2:5]([C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]3[O:20][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 15661966HCID 15661966, compound

Product 1

HCID 15661967HCID 15661967, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.43 g (12 mMol) of thionyl chloride are added dropwise at 10° C. with stirring to a suspension of 2.52 g (10 mMol) of 2-n-butyl-benzimidazole-5-carboxylic acid in 15 ml of N-methylpyrrolidinone. The mixture is stirred for a further 15 minutes at ambient temperature, then 1.31 g (11 mMol) of 2-aminophenol are added and the mixture is heated to 140° C. for 2 hours. The mixture is then poured onto about 50 g of ice and 5 ml of 30% sodium hydroxide solution are added with stirring. The crude product precipitated is suction filtered and purified by column chromatography (300 g of silica gel; eluant:methylene chloride+3% ethanol).

Workup

  1. temperaturethe mixture is heated to 140° C. for 2 hours
  2. additionare added
  3. stirringwith stirring
  4. customThe crude product precipitated
  5. filtrationfiltered
  6. custompurified by column chromatography (300 g of silica gel; eluant:methylene chloride+3% ethanol)

Sources & evidence

ORD record
ord-e82a928633ce46feba6ed3d031f7aa68
Source dataset
uspto-grants-1996_12
Patent number
US05587393

Reaction notes

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