Triethylamine → HCID 178484369、化合物

HRID 1075678ノート

反応式

HRID 1075678 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(OC([NH:37][C:38]([N:40]([CH3:42])[CH3:41])=S)=O)(C)(C)C.C(OCC)(=O)C>CN(C=O)C.FC(F)(F)C(O)=O.Cl[Hg]Cl>[CH3:41][N:40]([CH3:42])[C:38](=[NH:37])[NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 450920251-t-Butoxycarbonyl-3,3-dimethylthioureaHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

生成物 1

HCID 178484369HCID 178484369、化合物収率 50%

試薬・触媒・溶媒 3

HCID 24085Mercuric Chloride触媒HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

To a solution of 5-amino-3-(4-quinolylmethylen) -2-oxindole (431 mg, 1.5 mmol) in DMF (100 ml) containing triethylamine (202 mg, 2 mmol) was added 1-t-butoxycarbonyl-3,3-dimethylthiourea (409 mg, 2 mmol) and HgCl2 (543 mg, 2 mmol). The mixture was stirred at room temperature for 1 h and then filtered on a pad of celite. The residue was washed with ethyl acetate, the organic layer washed several times with water, dried and evaporated to dryness. The residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1. The above obtained BOC-derivative was taken up in trifluoroacetic acid (10 ml) and then stirred for 1 h at room temperature. Ethyl acetate was added, the organic layer washed with 1N sodium hydroxide and brine, dried and evaporated. The residue was chromatographed on a LoBar RP18 column with water as eluant to give pure title compound after freeze-drying. Yield 50% (268 mg).

後処理

  1. filtrationfiltered on a pad of celite
  2. washThe residue was washed with ethyl acetate
  3. washthe organic layer washed several times with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1
  7. customThe above obtained BOC-derivative
  8. stirringstirred for 1 h at room temperature
  9. washthe organic layer washed with 1N sodium hydroxide and brine
  10. customdried
  11. customevaporated
  12. customThe residue was chromatographed on a LoBar RP18 column with water as eluant

出典と根拠

ORDレコード
ord-40844b03e22c4d1bbb85c3fbe6bee499
出典データセット
uspto-grants-1999_05
特許番号
US05905149

反応ノート

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