Hydrogen Peroxide → 5,5-Dioxo-2-(6-methylpyridazin-3-ylamino)dibenzothiophene

HRID 1064012노트

반응식

HRID 1064012 반응식
OO.[CH3:3][C:4]1[N:9]=[N:8][C:7]([NH:10][C:11]2[CH:23]=[CH:22][C:14]3S[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:13]=3[CH:12]=2)=[CH:6][CH:5]=1.[S:24](=[O:28])(=O)(O)[OH:25]>C(O)(=O)C.C(Cl)Cl.CO>[O:25]=[S:24]1(=[O:28])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:16][C:17]=2[C:13]2[CH:12]=[C:11]([NH:10][C:7]3[N:8]=[N:9][C:4]([CH3:3])=[CH:5][CH:6]=3)[CH:23]=[CH:22][C:14]1=2

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 222777962-(6-Methylpyridazin-3-ylamino)dibenzothiophene

생성물 1

HCID 222778115,5-Dioxo-2-(6-methylpyridazin-3-ylamino)dibenzothiophene

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
60 °C

실험 절차

Hydrogen peroxide (100 vols, 1 ml) was added to 2-(6-methylpyridazin-3-ylamino)dibenzothiophene (Example 74; 300 mgs, 1.03 mmol) in acetic acid (3 ml) and conc. sulphuric acid (0.1 ml) and the mixture was heated to 60° C. for 40 minutes. On cooling to room temperature the mixture was diluted with DCM:MeOH (1:19) washed with aqueous potassium carbonate, dried over sodium sulphate and concentrated. Chromatography (eluent gradient of DCM to DCM:MeOH(1:1)) gave the product as an off white solid (0.131 g). NMR: 9.87 (brs, 1H), 8.48 (brs, 1H), 8.00-7.70 (m, 5H), 7.65 (t, 1H), 7.45 (d, 1H), 7.20 (d, 1H), 2.52 (s, 3H); m/z 324.28.

후처리

  1. temperatureOn cooling to room temperature the mixture
  2. washwashed with aqueous potassium carbonate
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-588e440825b9489d8f88b95b98289262
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967216B2

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