Sodium Acetate → HCID 21082405, compound

HRID 882936Notes

Reaction equation

HRID 882936 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([N+:14]([O-])=O)[C:5]=1[S:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([O-])=O.C([O-])(=O)C.[Na+]>CCO>[NH2:14][C:6]1[CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=[C:4]([NH2:1])[C:5]=1[S:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 58604119HCID 58604119, compound

Product 1

HCID 21082405HCID 21082405, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

Dinitro compound 12 (20 mmol) and sodium acetate (200 mmol) were added to 50 ml EtOH. The mixture was heated to 78° C., and the solid dissolved completely. Stannous chloride dihydrate (200 mmol) was added to the solution, and the reaction mixture was stirred at 7° C. for 35 minutes. After removal of solvent under reduced pressure, the residue was dissolved in 800 ml EtOAc, and washed with 40% KCO3. The organic phase was dried, evaporated and the residue column chromatographed (SiO2) and eluted with a gradient of CH2Cl2/MeOH from 100:1 to 95:5 to produce 13 in 93% yield. 1H NMR. (500 MHz, CDCl3): δ 6.21 (s, 2H), 5.41 (s, 1H), 4.35 (br, 4H), 3.21 (t, 2H), 2.75 (t, 2H), 1.35 (s, 9H), 1.24 (s, 9H). ESI-MS: m/z: 340.5 (MH+)

Workup

  1. dissolutionthe solid dissolved completely
  2. customAfter removal of solvent under reduced pressure
  3. dissolutionthe residue was dissolved in 800 ml EtOAc
  4. washwashed with 40% KCO3
  5. customThe organic phase was dried
  6. customevaporated
  7. customthe residue column chromatographed (SiO2)
  8. washeluted with a gradient of CH2Cl2/MeOH from 100:1 to 95:5

Sources & evidence

ORD record
ord-3c31eda8c76d4af68d94d9071dc1f3e9
Source dataset
uspto-grants-2012_08
Patent number
US08236800B2

Reaction notes

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