Hydrogen Sulfide → HCID 21216805, compound

HRID 1586441Notes

Reaction equation

HRID 1586441 reaction equation
[SH2:1].[C:2]1([CH2:8][CH2:9][C:10]([CH:19]([CH3:21])C)([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:11]#[N:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](NCC)C>C1(C)C=CC=CC=1>[C:2]1([CH2:8][CH2:9][C:10]([CH2:19][C:21]#[CH:22])([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:11](=[S:1])[NH2:12])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8021Diethylamine2×HCID 21216814HCID 21216814, compound

Product 1

HCID 21216805HCID 21216805, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A slow, steady stream of hydrogen sulfide was passed into a toluene solution (75 ml) of α-(2-phenylethyl)-α-(2-propyl)-3-pyridineacetonitrile (3.5 g) in the presence of diethylamine (1 ml). More diethylamine was added at the end of 1 hour (0.5 ml) and 3 hours (0.5 ml). The resultant reaction mixture was then evaporated to dryness and the residue dissolved in methylene chloride and washed with saturated sodium bicarbonate and water. After washing, the remaining organic extract was dried over sodium sulfate and worked up to give a solid. Recrystallization with hexanes produced α-(2-phenylethyl)-α-(2-propynyl)-3-pyridinethanethioamide with a melting point of 73-74° C.

Workup

  1. customThe resultant reaction mixture
  2. customwas then evaporated to dryness
  3. dissolutionthe residue dissolved in methylene chloride
  4. washwashed with saturated sodium bicarbonate and water
  5. washAfter washing
  6. extractionthe remaining organic extract
  7. dry with materialwas dried over sodium sulfate
  8. customto give a solid
  9. customRecrystallization with hexanes

Sources & evidence

ORD record
ord-07194ac48dc34dc3b853bfb85e59bb9f
Source dataset
uspto-grants-1999_08
Patent number
US05945436

Reaction notes

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