HCID 59783772, compound → HCID 59783830, compound

HRID 1946594Notes

Reaction equation

HRID 1946594 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[S:13][C:14](C(O)=O)=[CH:15][C:4]=2[NH:3]1>C(O)(=O)C>[S:13]1[C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[NH:3][C:4]=2[CH:15]=[CH:14]1

Participants

3

Reactant 1

HCID 59783772HCID 59783772, compound

Product 1

HCID 59783830HCID 59783830, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirring solution of compound 120 (0.801 g, 3.07 mmol) in acetic acid (30 mL) was added mercuric oxide (red) (0.664 g, 3.07 mmol) and the reaction mixture was stirred at reflux for 8 hours. The mixture was then cooled to room temperature and poured into ice-cold water (75 mL). The resulting solid was filtered and triturated in ethanol to afford title compound 121 (0.527 g, 79%) as a beige solid. LRMS (ESI): (calc) 217.02 (found) 217.9 (MH)+. 1H NMR (DMSO-d6) δ (ppm): 10.45 (s, 1H), 7.80 (d, J=7.6 Hz, 1H), 7.59 (t, J=7.2 Hz, 1H), 7.33 (t, J=7.4 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 6.99 (d, J=6.1 Hz, 1H), 6.63 (d, J=6.1 Hz, 1H).

Workup

  1. temperatureat reflux for 8 hours
  2. filtrationThe resulting solid was filtered
  3. customtriturated in ethanol

Sources & evidence

ORD record
ord-50a9560cd72a490da9527427f8d35be2
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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