Hydrogen Peroxide → HCID 22277831, compound

HRID 1064004Notes

Reaction equation

HRID 1064004 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([C:10]([NH:12][C:13]2[CH:25]=[CH:24][C:16]3S[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:15]=3[CH:14]=2)=[O:11])[CH3:9])=[CH:3][CH:2]=1.[S:26](=[O:30])(=O)(O)[OH:27].OO.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[O:27]=[S:26]1(=[O:30])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:18][C:19]=2[C:15]2[CH:14]=[C:13]([NH:12][C:10]([CH:8]([CH3:9])[CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:11])[CH:25]=[CH:24][C:16]1=2

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22277840HCID 22277840, compound

Product 1

HCID 22277831HCID 22277831, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-[(2-Pyrid-4-yl-1-methylethyl)carbonylamino]dibenzothiophene (Example 11; 0.39 g, 1.13 mmol) was dissolved in glacial acetic acid (10 ml) and concentrated sulphuric acid (0.5 ml) at 60° C. 30% aqueous hydrogen peroxide (1.3 ml) was added in one portion and the solution was stirred at 60° C. for two hours. The mixture was allowed to cool and then poured into water (50 ml). The mixture was made basic by the addition of solid NaHCO3 and extracted with DCM (2×50 ml). The combined organic layers were washed with brine (50 ml), dried and evaporated in vacuo to leave a pale yellow solid. NMR: 8.45 (d, 2H), 8.3 (d, 1H), 8.0 (d, 1H), 7.95 (d, 1H), 7.9 (d, 1H), 7.8 (t, 1H), 7.7 (dd, 1H), 7.65 (t, 1H), 7.25 (d, 2H), 3.0 (m, 2H), 2.7 (m, 1H), 1.15 (d, 3H); m/z 379.

Workup

  1. customat 60° C
  2. temperatureto cool
  3. extractionextracted with DCM (2×50 ml)
  4. washThe combined organic layers were washed with brine (50 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customto leave a pale yellow solid

Sources & evidence

ORD record
ord-ead93a81ee0647eba4a8c2d5b5a49688
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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