Triethylamine → 5,5-Dioxo-2-(isopropylcarbonylamino)dibenzothiophene

HRID 2055310ノート

反応式

HRID 2055310 の反応式
[O:1]=[S:2]1(=[O:16])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][C:3]1=2.C(N(CC)CC)C.[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26]>C(Cl)Cl>[O:1]=[S:2]1(=[O:16])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:24]([CH:25]([CH3:27])[CH3:26])=[O:28])[CH:13]=[CH:14][C:3]1=2

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 149185295,5-Dioxo-2-aminodibenzothiophene

生成物 1

HCID 693172165,5-Dioxo-2-(isopropylcarbonylamino)dibenzothiophene収率 46.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5,5-Dioxo-2-aminodibenzothiophene (J Med Chem, (1994), 37 (13), 2085-9; 231 mg, 1.0 mmol) was suspended in a solution of DCM (10 ml) and triethylamine (111 mg, 1.1 mmol). iso-Butyrylchloride (106.5 mg, 1.0 mmol) was added dropwise and the resultant mixture was stirred for 16 hours at ambient temperature. The mixture was evaporated in vacuo and the residue was purified by chromatography (Bond Elut column) eluting with 0-2.5% methanol in DCM to give the product as a colourless solid (139 mg). NMR: 10.38 (brs, 1H), 8.37 (s, 1H), 7.85-8.00 (m, 3H), 7.80 (d, 1H), 7.74 (d, 1H), 7.63 (t, 1H), 2.66 (m, 1H), 1.13 (d, 6H); m/z 302.

後処理

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by chromatography (Bond Elut column)
  3. washeluting with 0-2.5% methanol in DCM

出典と根拠

ORDレコード
ord-819015c7fc6d4f9ab1a5524de2846ae6
出典データセット
uspto-grants-2008_02
特許番号
US07332492B2

反応ノート

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