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

HRID 2193843Notes

Reaction equation

HRID 2193843 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 precipitate was collected, washed with water and a small amount of EtOH and 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 precipitate was collected
  7. washwashed with water
  8. dry with materiala small amount of EtOH and dried

Sources & evidence

ORD record
ord-076bda66166249b6a89be6e2a73b7662
Source dataset
uspto-grants-2012_12
Patent number
US08329914B2

Reaction notes

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