Toluene → HCID 131736041, compound

HRID 1049733Notes

Reaction equation

HRID 1049733 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[N+:17]([O-:19])=[O:18])(=O)=O.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][NH2:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O>[C:22]([O:26][C:27](=[O:28])[NH:29][CH2:30][CH2:31][NH:32][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[N+:17]([O-:19])=[O:18])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 187201N-BOC-ethylenediamineHCID 147652731-Nitronaphthalen-2-yl triflate

Product 1

HCID 131736041HCID 131736041, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Nitro-2-naphthyl trifluoromethanesulfonate (1.61 g, 5 mmol), N-(tert-butoxycarbonyl)ethylenediamine (0.80 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol), and toluene (20 mL) were mixed, and the mixture was refluxed by heating for 16 hours. This reaction mixture was added with water, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give yellow crystals, and the crystals were washed twice with hexane (20 mL) to obtain the title compound (1.50 g, yield 91%) as yellow crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give yellow crystals
  8. washthe crystals were washed twice with hexane (20 mL)

Sources & evidence

ORD record
ord-f00e57071df04048bd590e76485b882b
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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