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

HRID 2055310노트

반응식

HRID 2055310 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-819015c7fc6d4f9ab1a5524de2846ae6
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332492B2

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