Sodium Hydroxide → HCID 86722013, compound

HRID 524968Notes

Reaction equation

HRID 524968 reaction equation
[OH-].[Na+].[OH-].[NH4+:4].[Cl-].[NH4+].[Cl:7][C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[O:14].Cl[O-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(OCC)C.C(OC)(C)(C)C.C(OCC)(=O)C>[NH2:4][N:10]1[CH:11]=[CH:12][C:8]([Cl:7])=[C:9]1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[O:14]

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 23665760Sodium HypochloriteHCID 70922464HCID 70922464, compound

Product 1

HCID 86722013HCID 86722013, compoundYield 86%

Reagents, catalysts & solvents 4

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

In a 100 mL three-necked flask it was placed 11 mL of a 28% aqueous solution of sodium hydroxide, 4.1 mL of a 28% ammonium hydroxide solution, 1.23 g of ammonium chloride and 0.12 mL of Aliquat 336. Afterwards, a solution of 3-chloro-N-o-tolyl-1H-pyrrole-2-carboxamide (0.9 g, 3.84 mmol) in 30 mL of diethyl ether and 30 mL of methyl tert-butyl ether was added and placed at 0° C. affording a suspension. Over this suspension, a 10% aqueous solution of sodium hypochlorite (26 mL) was added drop wise with vigorous stirring maintaining the temperature during 20 min. more. Subsequently, the reaction mixture was stirred at room temperature during a further 1.5 h producing the consumption of the starting material. Next, the reaction crude was diluted with ethyl acetate until no suspended material was observed. The layers were separated and the organic phase was washed with a 25% aqueous solution of sodium thiosulphate, water and brine, dried (Na2SO4) and concentrated under vacuum to give a residue that was triturated with hexane to produce a solid (870 mg, 86% yield) after filtration.

Workup

  1. customIn a 100 mL three-necked flask it was placed
  2. customplaced at 0° C.
  3. customaffording a suspension
  4. temperaturemaintaining the temperature during 20 min. more
  5. stirringSubsequently, the reaction mixture was stirred at room temperature during a further 1.5 h
  6. customproducing
  7. customthe consumption of the starting material
  8. customNext, the reaction crude
  9. customThe layers were separated
  10. washthe organic phase was washed with a 25% aqueous solution of sodium thiosulphate, water and brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated under vacuum
  13. customto give a residue that
  14. customwas triturated with hexane

Sources & evidence

ORD record
ord-55333e27c0a44a06bd1c0ae09c7b9862
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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