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

HRID 1825850노트

반응식

HRID 1825850 반응식
[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]

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 11528611HCID 11528611, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d649a37378234ea183ec6d76a17e7d3d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049321B2

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