Lawesson's reagent → Methyl 4-amino-4-thioxobutanoate

HRID 2269706Notes

Reaction equation

HRID 2269706 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:30][CH3:31])(=[O:29])[CH2:24][CH2:25][C:26]([NH2:28])=O>C1(C)C=CC=CC=1>[NH2:28][C:26](=[S:10])[CH2:25][CH2:24][C:23]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 12550576Methyl 3-carbamoylpropanoate

Product 1

HCID 18333020Methyl 4-amino-4-thioxobutanoateYield 42.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (2.6 g) was added to a toluene (10 ml) solution of methyl succinamate (1.7 g). The reaction mixture was heated under reflux for 4 hours, cooled, and then concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain the entitled compound (400 mg) as an oily substance.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-bd80e97a080b4e869ebb685a9e91765b
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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