Stannous chloride dihydrate → HCID 68588616, compound

HRID 1496816Notes

Reaction equation

HRID 1496816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-])=O)=[C:8]([CH3:16])[CH:7]=1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[C:8]([CH3:16])[CH:7]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 68588944HCID 68588944, compound

Product 1

HCID 68588616HCID 68588616, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 18.00 g (57.6 mmol) of 4-(3,4-dichlorophenoxy)-2,5-dimethylnitrobenzene in 40 ml of dioxane and 40 ml of hydrochloric acid is admixed with 39.0 g (173.0 mmol) of tin(II) chloride dihydrate at room temperature and then refluxed for 2 h. It is cooled to room temperature, neutralized with NaHCO3 and extracted repeatedly with dichloromethane, and the extracts are dried over Na2SO4 and filtered, and the solvent is removed under reduced pressure (18.3 g, 89% purity, 99.5% yield, log P (pH 2.3)=3.51).

Workup

  1. temperaturerefluxed for 2 h
  2. extractionextracted repeatedly with dichloromethane
  3. dry with materialthe extracts are dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure (18.3 g, 89% purity, 99.5% yield, log P (pH 2.3)=3.51)

Sources & evidence

ORD record
ord-28bd493709d54b20a6ba79b7b4dd0575
Source dataset
uspto-grants-2015_12
Patent number
US09199922B2

Reaction notes

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