Water → HCID 86617109, compound

HRID 1723697Notes

Reaction equation

HRID 1723697 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([N:9]=[N+:10]=[N-:11])[CH2:7][N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[N:9]([C@@H:8]1[C@@H:4]([NH2:1])[CH2:5][N:6]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7]1)=[N+:10]=[N-:11]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 15479037HCID 15479037, compound

Product 1

HCID 86617109HCID 86617109, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step 4 (38.4 g, 158 mmol) in tetrahydrofuran (430 mL) was added triphenylphosphine (35.2 g, 134 mmol) and water (5.69 g, 316 mmol). The solution was stirred at room temperature until gas evolution had ceased and stirred at reflux for one hour. The reaction was cooled to RT and concentrated and the residue was dissolved in 4.0 N aqueous HCl (300 mL). The resultant mixture was extracted with chloroform (2×200 mL) and the aqueous phase was basified to pH 10 with concentrated aqueous ammonium hydroxide. This mixture was extracted with chloroform (3×300 mL) and the combined organic extracts were dried over sodium sulfate and concentrated to afford the 27.9 g (96%) of the product as an oil. MS m/z 218.3 (AP+100).

Workup

  1. stirringstirred
  2. temperatureat reflux for one hour
  3. temperatureThe reaction was cooled to RT
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in 4.0 N aqueous HCl (300 mL)
  6. extractionThe resultant mixture was extracted with chloroform (2×200 mL)
  7. extractionThis mixture was extracted with chloroform (3×300 mL)
  8. dry with materialthe combined organic extracts were dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4d5152a9b08743b485f1ebe44667ff08
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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