Ethanol → HCID 178423444, compound

HRID 916082Notes

Reaction equation

HRID 916082 reaction equation
[C:1]1([CH2:11][NH:12][C:13]2[CH:18]=C[C:16](C)=[CH:15][C:14]=2[NH2:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[SH-:21].[C+4:22].[SH-].[SH-].[SH-].[CH2:26](O)[CH3:27]>>[C:1]1([CH2:11][N:12]2[C:13]3[CH:18]=[C:26]([CH3:27])[CH:16]=[CH:15][C:14]=3[N:20]=[C:22]2[SH:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 17810729((1-Naphthyl)methyl)(2-amino-4-methyl-phenyl)amineHCID 178420937HCID 178420937, compound

Product 1

HCID 178423444HCID 178423444, compoundYield 44%

Procedure

Subsequently, ((1-naphthyl)methyl)(2-amino-4-methyl-phenyl)amine (943.1 mg, 3.59 mmol) was dissolved in ethanol (6.4 ml), to which carbon bisulfide (7 ml, 116 mmol) was added, and then refluxed. After 10 hours, it was returned to room temperature, concentrated under reduced pressure. Ethanol (2 ml) was added to the residue, which was stirred at room temperature for 30 minutes, and was further stirred on ice for 30 minutes. The resulting crystals were filtered, and dried to obtain 1-((1-naphthyl)methyl)-6-methyl-benzimidazole-2-thiol (459.1 mg, yield 44%, 2 steps).

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. customwas returned to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionEthanol (2 ml) was added to the residue, which
  6. stirringwas further stirred on ice for 30 minutes
  7. filtrationThe resulting crystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-24e62a9e4c214738bfaf1dc9e2a399eb
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

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