Carbon Disulfide → HCID 178423448, compound

HRID 1789200Notes

Reaction equation

HRID 1789200 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[NH2:8].[C:10](=S)=[S:11].[OH-].[Na+]>C(O)C>[SH:11][C:10]1[NH:1][C:2]2[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 103323,4-DiaminotolueneHCID 14798Sodium Hydroxide

Product 1

HCID 178423448HCID 178423448, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.2 g (0.1 mole) of 3,4-diaminotoluene, 35 ml of carbon disulfide, and 4.0 g (0.1 mole) of sodium hydroxide was heated at reflux in 350 ml of ethanol. After 2.5 hours the mixture was concentrated in vacuo. The residue was suspended in 200 ml of 4% aqueous hydrochloric acid, collected by filtration, washed sequentially with water and diethyl ether, and air dried to yield 12.2 g of 2-mercapto-5-methylbenzimidazole, as confirmed by the nmr and infrared spectra. The title compound (796 mg) was prepared by the method of Example 6 using 8-hydroxymethylimidazo[1,2-a]pyridine as the hydrochloride salt and using 569 mg (3.5 mmole) of 2-mercapto-5-methylbenzimidazole instead of 2-mercapto-5-methoxybenzimidazole. Structure assignment was supported by elemental analysis.

Workup

  1. temperaturewas heated
  2. concentrationAfter 2.5 hours the mixture was concentrated in vacuo
  3. filtrationcollected by filtration
  4. washwashed sequentially with water and diethyl ether, and air
  5. customdried

Sources & evidence

ORD record
ord-a6c6686884974bc0978bd9d303374472
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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