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

HRID 1397331Notes

Reaction equation

HRID 1397331 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 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl succinamate (2.5 g, 0.019 mol) in THF (60 mL) was cooled to 0° C. and P2S5 (4.2 g, 0.019 mol) was added. The reaction mixture was warmed to room temperature and stirred for 6 h. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 35-40% EtOAc in petroleum ether) to afford methyl 4-amino-4-thioxobutanoate (1.6 g, yield 57%). 1H NMR (300 MHz, CDCl3) δ 7.49 (br s, 2H), 3.72 (s, 3H), 2.95-2.86 (m, 4H). MS (ESI) m/z: Calculated for C5H9NO2S: 147.04. found: 248.2 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 35-40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-bb3dfd7ea8f841e38ac114324f0bfc5c
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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