Carbon Disulfide → HCID 178488032, compound

HRID 1030572Notes

Reaction equation

HRID 1030572 reaction equation
[OH-].[K+].[C:3](=[S:5])=S.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([NH2:15])[CH:9]=1>C(O)C.O.C(Cl)Cl>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]2[N:14]=[C:3]([SH:5])[NH:15][C:10]=2[CH:9]=1

Participants

7

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 1534044-Methoxy-o-phenylenediamine

Product 1

HCID 178488032HCID 178488032, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To potassium hydroxide (3.8 g, 0.067M) in ethanol (20 mL) and water (7 mL) was added 2.5 mL CS2 (3.09 g, 0.04M) (H2S trapped over clorox). The reaction mixture was stirred for 30 minutes at ambient temperature, cooled to 0° C., and 4-methoxy-o-phenylene diamine (5.23 g, 0.03M) was slowly added. This reaction mixture was then stirred at reflux for 4 hours, stirred at ambient temperature overnight (basic soln. with pH paper), evaporated in vacuo and diluted with CH2Cl2. Addition of water gave a precipitate which was suspended in CH2Cl2 and acidified to pH 4. Filtration of the suspension gave purple crystalline 5-methoxy-2-mercaptobenzimidazole (3.4 g, 63%).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThis reaction mixture was then stirred
  3. temperatureat reflux for 4 hours
  4. stirringstirred at ambient temperature overnight (basic soln. with pH paper)
  5. customevaporated in vacuo
  6. additiondiluted with CH2Cl2
  7. additionAddition of water
  8. customgave a precipitate which
  9. filtrationFiltration of the suspension

Sources & evidence

ORD record
ord-9ff27216e84b4e30af3c3c5846bf63ee
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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