Carbon Disulfide → 5-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione

HRID 340765Notes

Reaction equation

HRID 340765 reaction equation
[OH-].[K+].[C:3](=[S:5])=S.[Cl:6][C:7]1[CH:8]=[C:9]([NH2:15])[C:10]([NH2:14])=[CH:11][C:12]=1[I:13]>O.CCO>[Cl:6][C:7]1[C:12]([I:13])=[CH:11][C:10]2[NH:14][C:3](=[S:5])[NH:15][C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 574814674-Chloro-5-iodobenzene-1,2-diamine

Product 1

HCID 574814685-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (15.7 g, 238 mmol) in water (50 mL), followed by carbon disulfide (14.4 mL, 238 mmol), was added to a solution of 4-chloro-5-iodobenzene-1,2-diamine (50 g, 198 mmol) in EtOH (300 mL). The mixture was heated at reflux for 3 h, cooled and filtered. To the filtrate was added water (300 mL) and then AcOH (25 mL) in water (50 mL). The resulting precipitate was collected, washed with water and a small amount of EtOH, and then dried to afford the desired product as a brown powder, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled
  4. filtrationfiltered
  5. additionTo the filtrate was added water (300 mL)
  6. customThe resulting precipitate was collected
  7. washwashed with water
  8. dry with materiala small amount of EtOH, and then dried

Sources & evidence

ORD record
ord-5a0e54d45a22476889bb42ebe2729721
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

Loading…