2-Aminophenol → HCID 10904161, compound

HRID 1636971Notes

Reaction equation

HRID 1636971 reaction equation
[CH2:1]([CH:3]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:14])[CH3:2].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26].[S]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:14]1[O:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=1)[CH3:2]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 5362487SulfurHCID 10911774HCID 10911774, compound

Product 1

HCID 10904161HCID 10904161, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

24.4 g (0.1 mol) of 1-(2-ethylhexyl)-2-methylbenzimidazole (prepared by heating N-2-ethylhexyl-o-phenylenediamine in acetic acid/hydrochloric acid), 10.9 g (0.1 mol) of o-aminophenol and 9.6 g (0.3 mol) of sulfur in 100 ml of pyridine are heated under reflux for 18 hours. After cooling to room temperature, the crude product is precipitated by addition of water. Multiple recrystallization from n-hexane with addition of active charcoal gives 5.7 g (16% of theory) of product, which according to melting point, HPLC and UV determination is identical to the compound obtained in Example 7.

Workup

  1. temperatureunder reflux for 18 hours
  2. customthe crude product is precipitated by addition of water
  3. customrecrystallization from n-hexane
  4. additionwith addition of active charcoal
  5. customgives 5.7 g (16% of theory) of product, which

Sources & evidence

ORD record
ord-918ec91f7f1246248be69325547facc7
Source dataset
uspto-grants-2000_03
Patent number
US06037473

Reaction notes

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