Stannous chloride dihydrate → HCID 22016066, compound

HRID 2363675Notes

Reaction equation

HRID 2363675 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([N:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][CH:10]=[CH2:11])=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>CCO>[CH2:12]([N:8]([CH2:9][CH:10]=[CH2:11])[C:7]1[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][CH:6]=1)[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 11579422HCID 11579422, compound

Product 1

HCID 22016066HCID 22016066, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-nitro-N,N-di(prop-2-en-1-yl)aniline (12.22 g, 55.98 mmol) and tin (II) chloride dihydrate (64.45 g, 279.9 mmol) in EtOH (280 ml) was stirred and heated under reflux for 21 h. The cooled reaction mixture was concentrated under reduced pressure to a volume of 100 ml, and neutralised by the addition of 5 M NaOH. The precipitate was removed by filtration and the filtrate was extracted with EtOAc (4×200 ml). The combined organics were washed with brine (2×200 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown oil that was purified by chromatography (1:1 Hexane/EtOAc) to give the title compound (7.79 g, 74%) as a brown oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 21 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated under reduced pressure to a volume of 100 ml
  5. additionneutralised by the addition of 5 M NaOH
  6. customThe precipitate was removed by filtration
  7. extractionthe filtrate was extracted with EtOAc (4×200 ml)
  8. washThe combined organics were washed with brine (2×200 ml)
  9. dry with materialdried (Na2SO4)
  10. customThe solvent was removed under reduced pressure
  11. customto give a brown oil that
  12. customwas purified by chromatography (1:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-5545f5a0af014ee789f4705b5c791372
Source dataset
uspto-grants-2014_04
Patent number
US08691979B2

Reaction notes

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