Lawesson's reagent → 2-Ethyl-8-methyl-1-thia-4,8-diaza-spiro[4.5]decane-3-thione

HRID 1825850ノート

反応式

HRID 1825850 の反応式
[CH3:1][CH2:2][CH:3]1[S:8][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[NH:6][C:4]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C(#N)C>[CH2:2]([CH:3]1[C:4](=[S:24])[NH:6][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[S:8]1)[CH3:1]

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 11528611HCID 11528611、化合物

生成物 1

HCID 104664182-Ethyl-8-methyl-1-thia-4,8-diaza-spiro[4.5]decane-3-thione

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of AF267 (214 mg, 1 mmol) and Lawesson's Reagent (280 mg, 0.692 mmol) in acetonitrile (5 ml) was heated under reflux for 17 hrs. The solvent was removed and residue was dissolved in concentrate aqueous sodium carbonate (0.5 ml) and then extracted with ethyl acetate. The extract was dried and the solvent evaporated. The residue (250 mg), recrystallized first from toluene and then from acetonitrile gave pure AF510. 1H-NMR (CDCl3) δ 1.03 (t, CH3CH2), 1.83 (m), 1.93–2.44 (m), 2.30 (s, CH3N), 2.80 (m, 2H), 4.21 (dd, SCH), 8.66 (br, NH) ppm. MS m/e 230 (M30), 197 (M+−SH), 156, 128, 96 (100%).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hrs
  3. customThe solvent was removed
  4. dissolutionresidue was dissolved in concentrate aqueous sodium carbonate (0.5 ml)
  5. extractionextracted with ethyl acetate
  6. customThe extract was dried
  7. customthe solvent evaporated
  8. customThe residue (250 mg), recrystallized first from toluene
  9. customfrom acetonitrile gave pure AF510

出典と根拠

ORDレコード
ord-d649a37378234ea183ec6d76a17e7d3d
出典データセット
uspto-grants-2006_05
特許番号
US07049321B2

反応ノート

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