Sodium Carbonate → HCID 49764091, compound

HRID 468572Notes

Reaction equation

HRID 468572 reaction equation
[CH2:1]([N:28]1[C:32]([CH3:34])([CH3:33])[C:31](=[O:35])[N:30]([C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[C:38]([C:45]([F:48])([F:47])[F:46])[CH:37]=2)[C:29]1=[O:49])[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=2)[C:7]1=[O:27].Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.CCCCCCC.CCOC(C)=O>[CH2:5]([N:6]1[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=2)[C:7]1=[O:27])[CH2:4][CH2:3][CH2:2][CH2:1][N:28]1[C:32]([CH3:34])([CH3:33])[C:31](=[O:35])[N:30]([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([C:45]([F:46])([F:47])[F:48])[CH:37]=2)[C:29]1=[O:49]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 46937259HCID 46937259, compound

Product 1

HCID 49764091HCID 49764091, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the compound of Example 2 (410 mg, 0.58 mmole) and SnCl2, 2H2O (1.32 g, 5.8 mmoles) in AcOEt (10 ml) is heated at 80° C. for 90 minutes. The reaction medium is then cooled down to 0° C. before being poured into a saturated aqueous solution of Na2CO3 (40 ml). The heterogeneous mixture thus obtained is filtered on celite and rinsed with AcOEt (2×50 ml). After decantation, the organic phases are combined, dried over Na2SO4, filtered and the solvent is evaporated off under reduced pressure. The residue obtained is taken up in a mixture of heptane/AcOEt in order to produce a white solid, after filtration, with a yield of 78% (290 mg). Melting point: 108-109° C.

Workup

  1. temperatureThe reaction medium is then cooled down to 0° C.
  2. customThe heterogeneous mixture thus obtained
  3. filtrationis filtered on celite
  4. washrinsed with AcOEt (2×50 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe residue obtained
  9. customto produce a white solid
  10. filtrationafter filtration

Sources & evidence

ORD record
ord-cd4f1252c74d4b14b7a7e9846171b77f
Source dataset
uspto-grants-2014_01
Patent number
US08624037B2

Reaction notes

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