Hydrochloric Acid → Triphenylphosphine

HRID 432703Notes

Reaction equation

HRID 432703 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=C(CCC[O:29]CCN2C3C4C(=CC=CC=4)N4N=NN=C4C=3N=C2)C=1.Cl.O>ClC1C=CC=CC=1Cl>[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:14]1([P:7](=[O:29])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 187601846-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline

Product 2

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Triphenylphosphine (27.0 g, 115 mmol) was added to a solution of 6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline (28.7 g, 76.9 mmol) in 1,2-dichlorobenzene (1 L). The reaction was heated at reflux temperature overnight. The dark red solution was cooled to room temperature and treated with 1N HCl (225 ml). A tan precipitate formed. The resulting mixture was concentrated in vacuo to yield a dark red/brown solid. This material was treated with 500 ml water and vigorously stirred. Excess triphenylphosphine and triphenylphosphine oxide formed as precipitates and were removed by vacuum filtration. The solid was washed with several portions of water followed by a final wash with dilute HCl (1:5, 1N HCl:water). The red/brown filtrate was collected, washed with ether (3×150 ml), and treated with 10% NaOH solution until the pH reached 12. The crude product formed as a tan precipitate and was collected by filtration. Purification of the crude material was accomplished by treatment (2×) with activated charcoal (Darco-G60) in refluxing methanol. The charcoal was removed by filtration. The desired product formed as a precipitate during concentration of the filtrate.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux temperature overnight
  3. customA tan precipitate formed
  4. concentrationThe resulting mixture was concentrated in vacuo
  5. customto yield a dark red/brown solid

Sources & evidence

ORD record
ord-375040f962e64e01be06935a7999f233
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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