Potassium Hydroxide → HCID 22629950, compound

HRID 2306878Notes

Reaction equation

HRID 2306878 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:4]=1[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].O.O.[Sn](Cl)[Cl:30].[OH-].[K+]>C(O)C.O>[ClH:30].[NH2:24][C:21]1[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[C:4]([CH:20]=1)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 10309289HCID 10309289, compound

Product 1

HCID 22629950HCID 22629950, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product of Example 11 dissolved in ethanol and treated with 4 equivalents of Tin(II) dichloride dihydrate at reflux for 4 h. The reaction was cooled, diluted with water, made basic with potassium hydroxide and extracted with ethyl acetate (3×250 mL). The combined organics were washed with water then saturated sodium chloride solution. The solvent was removed in vacuo and the residue dissolved in diethyl ether. 4 N HCl in dioxane was added in excess and the resulting precipitate was filtered by suction to afford the product. 345.2 M+1

Workup

  1. temperatureat reflux for 4 h
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate (3×250 mL)
  4. washThe combined organics were washed with water
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in diethyl ether
  7. addition4 N HCl in dioxane was added in excess and the resulting precipitate
  8. filtrationwas filtered by suction
  9. customto afford the product

Sources & evidence

ORD record
ord-fa8faa7a9ac64ca6a9f01b5a1a82f57a
Source dataset
uspto-grants-2004_12
Patent number
US06828446B2

Reaction notes

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