Stannous Chloride → HCID 59497060, compound

HRID 1878515Notes

Reaction equation

HRID 1878515 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=[C:4]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[N:3]=1.[Sn](Cl)Cl>C(O)C>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][S:16][C:4]2[N:3]=[C:2]([Cl:1])[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 59497066HCID 59497066, compound

Product 1

HCID 59497060HCID 59497060, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2 (1.11 g) in ethanol (25 mL0 at room temperature was added tin(II) chloride dehydrate (3.81 g) and the resulting mixture was refluxed for 2 hours. After cooling to rt, the volume was reduce by approximately half by concentration in vacuo and the remaining clear yellow solution was poured into chilled saturated sodium bicarbonate solution. The resulting white suspension was treated with EtOAc and filtered through Celite. The filtrate was allowed to separate and the aqueous layer was extracted with EtOAc thrice. The combined organic extracts was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give crude 3 as an orange oil (1.12 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. concentrationthe volume was reduce by approximately half by concentration in vacuo
  3. additionthe remaining clear yellow solution was poured
  4. temperatureinto chilled saturated sodium bicarbonate solution
  5. additionThe resulting white suspension was treated with EtOAc
  6. filtrationfiltered through Celite
  7. customto separate
  8. extractionthe aqueous layer was extracted with EtOAc thrice
  9. washThe combined organic extracts was washed with water and brine
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11ab34bf542f42caaef31af129b11b6c
Source dataset
uspto-grants-2012_11
Patent number
US08314116B2

Reaction notes

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