Stannous Chloride → HCID 46944973, compound

HRID 2370591Notes

Reaction equation

HRID 2370591 reaction equation
Cl[Sn]Cl.[CH3:4][C:5]1([CH3:45])[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19][CH2:20][CH2:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:8](=[O:30])[N:7]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[C:33]([C:40]([F:43])([F:42])[F:41])[CH:32]=2)[C:6]1=[O:44].C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:37][C:34]1[CH:35]=[CH:36][C:31]([N:7]2[C:6](=[O:44])[C:5]([CH3:45])([CH3:4])[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19][CH2:20][CH2:21][CH2:22][C:23]([F:28])([F:29])[C:24]([F:25])([F:26])[F:27])[C:8]2=[O:30])=[CH:32][C:33]=1[C:40]([F:43])([F:42])[F:41]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 46947722HCID 46947722, compound

Product 1

HCID 46944973HCID 46944973, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

SnCl2, 2H2O (3.84 g, 17 mmoles) is added to the compound of Example 1 (1.08 g, 1.7 mmole) dissolved in AcOEt (30 ml). The reaction mixture is heated under reflux until the starting compound disappears (5 h 30) and then cooled down using an ice bath. After dilution with AcOEt (30 ml), the mixture is poured onto a 1M aqueous solution of NaHCO3 (120 ml). The mixture is stirred for a few hours during which time a white precipitate forms. This precipitate is eliminated by filtration on celite. The filtrate is decanted and the organic solution is dried over Na2SO4, filtered and concentrated to dryness under vacuum. The expected compound is obtained in the form of a yellow oil with a yield of 84% (868 mg).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux until the starting compound
  3. custom(5 h 30)
  4. temperaturecooled down
  5. filtrationThis precipitate is eliminated by filtration on celite
  6. customThe filtrate is decanted
  7. dry with materialthe organic solution is dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-347556575c6949e7a3bfd32ce3f27429
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

Loading…