Carbon Disulfide → HCID 178423448, compound

HRID 1071560Notes

Reaction equation

HRID 1071560 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, and the product was 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 (2.0 g) was prepared by the method of Example 84 using 1.6 g (9.7 mmole) of 2-mercapto-5-methylbenzimidazole instead of 2-mercaptobenzimidazole. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis. Analysis. Calc'd. for C14H14N4S: C, 60.19; H, 5.01; N,20.05; S, 11.47. Found: C, 59.80; H, 5.05; N, 20.00; S, 11.17.

Workup

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

Sources & evidence

ORD record
ord-422944edf7bc43d9a0dd533ae5b26a9f
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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