Carbon Disulfide → HCID 178504605, compound

HRID 452748Notes

Reaction equation

HRID 452748 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[C:16]([C:19]([NH:21][NH2:22])=[O:20])[CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)=[O:3].[C:23](=S)=[S:24].C(N(CC)CC)C.[OH-].[Na+]>C(O)C.O>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:20][C:23]([SH:24])=[N:22][N:21]=4)[CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 68664090HCID 68664090, compound

Product 1

HCID 178504605HCID 178504605, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-[4-(methylsulfinyl)phenyl]-1H-benzimidazole-6-carbohydrazide (1.26 g, 4.00 mmol), carbon disulfide (0.601 mL, 10.0 mmol) and triethylamine (0.669 mL, 4.80 mmol) in ethanol (20 mL) was heated under reflux for 3 hr. After cooling, the reaction mixture was poured into water, and alkalified with 1 M aqueous sodium hydroxide solution. The obtained aqueous solution was filtered, and the filtrate was neutralized with 1M hydrochloric acid. The precipitate was collected by filtration, and washed with ethanol to give the title compound (0.955 g, yield 67%) as colorless crystals.

Workup

  1. temperatureunder reflux for 3 hr
  2. temperatureAfter cooling
  3. filtrationThe obtained aqueous solution was filtered
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-a591eb78d5ae40298d1a67416de4773b
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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