Carbon Disulfide → HCID 178527934, compound

HRID 452690Notes

Reaction equation

HRID 452690 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:14](=S)=[S:15].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:14]([SH:15])=[N:13][N:12]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 185264692,3-Dihydro-1-benzofuran-5-carbohydrazide

Product 1

HCID 178527934HCID 178527934, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,3-dihydro-1-benzofuran-5-carbohydrazide (535 mg, 3.00 mmol), carbon disulfide (0.397 mL, 6.60 mmol) and triethylamine (0.460 mL, 3.30 mmol) in ethanol (5 mL) was heated under reflux for 24 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed with 0.1M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/tetrahydrofuran to give the title compound (529 mg, yield 80%) as pale-yellow crystals.

Workup

  1. temperatureunder reflux for 24 hr
  2. temperatureAfter cooling
  3. washwashed with 0.1M hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-0a80b7b5f1d244809210cc94eed67b6e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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