Hydrogen Sulfide → 2-(3,4-Dichlorophenyl)ethanethioamide

HRID 1643254Notes

Reaction equation

HRID 1643254 reaction equation
S.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]#[N:12])[CH:6]=[CH:7][C:8]=1[Cl:9].C(N(CC)CC)C.C(N)(=[S:22])C>C(O)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([NH2:12])=[S:22])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 2723949Thioacetamide

Product 1

HCID 215042642-(3,4-Dichlorophenyl)ethanethioamideYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen sulfide (gas) was bubbled into a solution of (3,4-dichloro-phenyl)-acetonitrile (1.86 g, 10 mmol, 1.0 eq)) and triethyl amine (10 mmol, 1 eq) in ethanol (10 ml) for about 1 hour. After 1 hour the reaction mixture capped and stirred at room temperature overnight. TLC showed that most of nitrile was converted to thioacteamide. Excess of H2S was removed by bubbling nitrogen into the reaction mixture for 30 min. The reaction mixture was then concentrated and purified by silica gel chromatography (ISCO system, 30-60% ethylacetate/hexane) to give the title compound (1213) (55% yield).

Workup

  1. customAfter 1 hour the reaction mixture capped
  2. customExcess of H2S was removed
  3. customby bubbling nitrogen into the reaction mixture for 30 min
  4. concentrationThe reaction mixture was then concentrated
  5. custompurified by silica gel chromatography (ISCO system, 30-60% ethylacetate/hexane)

Sources & evidence

ORD record
ord-b84096660d1c4f2b887343292b84a8bb
Source dataset
uspto-grants-2012_02
Patent number
US08119680B2

Reaction notes

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