Triphenylphosphine → N,N-Diethyl-N-[3-((6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl)oxy)propyl]amine

HRID 387856Notes

Reaction equation

HRID 387856 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[S:14][C:15]1[S:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1.[CH2:23]([N:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28]O)[CH3:24].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.CS(C)=O.CN1CCCC1=O.O1CCCC1>[CH2:23]([N:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([S:14][C:15]3[S:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1])[CH3:24]

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 121593-(Diethylamino)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1359899586-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinol

Product 1

HCID 58931471N,N-Diethyl-N-[3-((6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl)oxy)propyl]amineYield 74.7%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinol (500 mg), 3-diethylaminopropanol (290 mg), diethyl azodicarboxylate (390 mg), triphenylphosphine (590 mg), tetrahydrofuran (30 ml), 1-methyl-2-pyrrolidinone (2 ml) and dimethylsulfoxide (10 ml) were stirred together at 0° C. for 5 hours and then at room temperature for 10 hours. Water was added, extraction was performed with ethyl acetate, and the extract was back extracted with 2N aqueous hydrochloric acid. After adding 5N aqueous sodium hydroxide to the hydrochloric acid extract and performing extraction with ethyl acetate, the extract was washed with water and then with saline and dried over magnesium sulfate. NH type silica gel was coated onto a glass filter, the ethyl acetate layer was passed through the filter, and the solvent was distilled off under reduced pressure to obtain 500 mg of a reddish-brown oil.

Workup

  1. extractionextraction
  2. extractionthe extract was back extracted with 2N aqueous hydrochloric acid
  3. additionAfter adding 5N aqueous sodium hydroxide to the hydrochloric acid
  4. extractionextract
  5. extractionextraction with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialwith saline and dried over magnesium sulfate
  8. filtrationfilter
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dd4656478e5f4435b8f8e80d32add009
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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