Tin tetrachloride → HCID 86584206, compound

HRID 987029Notes

Reaction equation

HRID 987029 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16](=[CH2:30])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([N+:27]([O-])=O)[CH:21]=2)=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([C:16](=[CH2:30])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([NH2:27])[CH:21]=2)=[O:18])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 86600355HCID 86600355, compound

Product 1

HCID 86584206HCID 86584206, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

In a 100 ml flask equipped with a refrigerant, 0.9 g (2.18 mmoles) of 3-[(3,5-bis-(1,1-dimethylethyl) -4-hydroxyphenyl]-N-(4-hydroxy-3-nitrophenyl)-2-propenamide is dissolved in 20 ml of ethyl acetate, 2.46 g (10.9 mmoles) of tin chloride (dihydrate) is added and the mixture is heated at 70° C. for three hours. After returning to ambient temperature, the reaction medium is poured onto an agitated solution of sodium bicarbonate (0.1 M), a precipitate forms, which is eliminated by filtration on celite. The filtrate is decanted and the aqueous phase is extracted with 20 ml of ethyl acetate. The organic phases are collected together and washed with 20 ml of water followed by 20 ml of a saturated solution of sodium chloride. After drying over sodium sulphate and filtration, the organic solution is concentrated to dryness, under partial vacuum. The evaporation residue is suspended in a heptane/ethyl acetate mixture (1/1) and filtered to produce a yellowish powder with a yield of 53%. The product is used as it is in the following stage.

Workup

  1. customAfter returning to ambient temperature
  2. filtrationa precipitate forms, which is eliminated by filtration on celite
  3. customThe filtrate is decanted
  4. extractionthe aqueous phase is extracted with 20 ml of ethyl acetate
  5. customThe organic phases are collected together
  6. washwashed with 20 ml of water
  7. dry with materialAfter drying over sodium sulphate and filtration
  8. concentrationthe organic solution is concentrated to dryness, under partial vacuum
  9. filtrationfiltered
  10. customto produce a yellowish powder with a yield of 53%

Sources & evidence

ORD record
ord-acfa6247ba614a8ba9a9e5946b6e4da1
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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