Phosphorus sulfide (P2S5) → 2-(Thiophen-2-yl)ethanethioamide

HRID 52191

Reaction equation

HRID 52191 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH2:9])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:11]>C1COCC1>[CH:4]1[CH:3]=[C:2]([CH2:6][C:7]([NH2:9])=[S:11])[S:1][CH:5]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 78208Thiophen-2-acetamide

Product 1

HCID 53119242-(Thiophen-2-yl)ethanethioamideYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in THF (200 mL) of 2-thiopheneacetamide (4.04 g, 28.6 mmol), prepared as in step 1, was added P4S10 (12,7 g, 28.6 mmol), and the vigorously stirred reaction mixture was placed in a Bransonic 221 bath and irradiated with ultrasound for 30 min. The reaction mixture was filtered and the tiltrate was concentrated in vacuo. The crude product was taken up in CH2Cl2 and decanted from the solid residue. Pure 2-thiophenethioacetamide (2.45 g, 54% yield) was obtained by chromatography on silica gel (CH2Cl2).

Workup

  1. customthe vigorously stirred reaction mixture
  2. customirradiated with ultrasound for 30 min
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe tiltrate was concentrated in vacuo
  5. customdecanted from the solid residue

Sources & evidence

ORD record
ord-1a3a301158814011a8b1f5c2bda94702
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Linked notes

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