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

HRID 1720449Notes

Reaction equation

HRID 1720449 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 (20(3 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 sonicated with ultrasound for 30 min. The reaction mixture was filtered and the filtrate 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. customsonicated with ultrasound for 30 min
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customdecanted from the solid residue

Sources & evidence

ORD record
ord-38665fdd8efb4e24a472ed7b7b5ab5b1
Source dataset
uspto-grants-1996_04
Patent number
US05506261

Reaction notes

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