Phosphorus sulfide (P2S5) → Methyl 4-amino-4-thioxobutanoate

HRID 1397300Notes

Reaction equation

HRID 1397300 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([NH2:6])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:11]>C1COCC1>[NH2:6][C:4](=[S:11])[CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 12550576Methyl 3-carbamoylpropanoate

Product 1

HCID 18333020Methyl 4-amino-4-thioxobutanoateYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl succinamate (2 g, 15.2 mmol) was dissolved in dry THF (50 mL) and P2S5 (3.4 g, 15.2 mmol) was added and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was filtered through a sintered funnel and the clear filtrate was concentrated under reduced pressure to get the crude product, which was further purified by column chromatography (silica gel 60-120 mesh, eluent 50% EtOAc in petroleum ether) to afford methyl 4-amino-4-thioxobutanoate (1.25 g, yield 53%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.27 (br s, 2H), 3.72 (s, 3H), 2.96-2.85 (m, 4H). MS (ESI) m/z: Calculated for C5H9NO2S: 147.04. found: 148.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a sintered funnel
  2. concentrationthe clear filtrate was concentrated under reduced pressure
  3. customto get the crude product, which
  4. customwas further purified by column chromatography (silica gel 60-120 mesh, eluent 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-69f6d4b76c954659a7591d6102157aad
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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