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

HRID 1397300ノート

反応式

HRID 1397300 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 18333020Methyl 4-amino-4-thioxobutanoate収率 55.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-69f6d4b76c954659a7591d6102157aad
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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