Hydrogen Sulfide → HCID 14950598, compound

HRID 357622Notes

Reaction equation

HRID 357622 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])#[N:2].C(N(CC)CC)C.[SH2:20]>N1C=CC=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])(=[S:20])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 27515831-Oxo-2,3-Dihydro-1H-Indene-4-Carbonitrile

Product 1

HCID 14950598HCID 14950598, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 12.1 g (77 mmol) of 4-cyano-2,3-dihydro-1H-inden-1-one [see Coll. Czechoslov. Chem. Commun. 4, 3227 (1978)] in 220 ml of pyridine and 10.6 ml (77 mmol) of triethylamine is saturated with hydrogen sulfide for 3 hours at 40° and is then stirred at the same temperature for 16 hours. The reaction mixture is cooled and then concentrated to dryness by evaporation, and 300 ml of water are added to the residue. The yellow product that has crystallized out is filtered off with suction, washed with water, dried and recrystallized from ethyl acetate. In that manner there is obtained the title compound, m.p. 197° (decomp.).

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated to dryness by evaporation, and 300 ml of water
  3. additionare added to the residue
  4. customThe yellow product that has crystallized out
  5. filtrationis filtered off with suction
  6. washwashed with water
  7. customdried
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-101305402571408cb31c9881afa6b2f7
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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