Triethylamine → HCID 68851040, Verbindung

HRID 492287

Reaktionsgleichung

Reaktionsgleichung von HRID 492287
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[CH2:37]([NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]2[N:62]([C:63]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[N:61]=[N:60][N:59]=2)=[CH:48][CH:47]=1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>C1C=CC=CC=1>[CH2:37]([N:44]([CH2:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]2[N:62]([C:63]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)([C:76]3[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=3)[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[N:61]=[N:60][N:59]=2)=[CH:50][CH:51]=1)[C:35](=[O:20])[NH:32][C:3]1[C:7]([F:12])=[CH:8][C:9]([F:11])=[CH:10][C:2]=1[F:1])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5203732,4,6-Trifluorobenzoic acidHCID 68851238HCID 68851238, Verbindung

Produkt 1

HCID 68851040HCID 68851040, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

2,4,6-Trifluorobenzoic acid (148.8 mg), diphenylphosphoryl azide (223.3 mg) and triethylamine (105.1 mg) were added to benzene (8 mL) and the mixture was heated under reflux. Fifty minutes later, a solution of N-heptyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (393.7 mg) in benzene (3 mL) was added to the reaction mixture, and under reflux, heating was continued. Upon elapsed time of 45 minutes after the addition of the solution, the reaction mixture was concentrated under reduced pressure. Ethyl acetate (40 mL) was added to the residue, and the resulting mixture was washed successively with 5% hydrochloric acid, water, a saturated sodium bicarbonate solution and brine (40 mL, each). The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane/ethyl acetate) to afford N′-heptyl-N-(2,4,6-trifluorophenyl)-N′-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]urea as a colorless amorphous mass (369.1 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureunder reflux
  4. temperatureheating
  5. additionUpon elapsed time of 45 minutes after the addition of the solution
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionEthyl acetate (40 mL) was added to the residue
  8. washthe resulting mixture was washed successively with 5% hydrochloric acid, water
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b98e816bba8844feb006a99d8dff52de
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531576B2

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