Triethylamine → 1-(2-Chlorophenyl)-3-[1-(1-naphthyl)tetrazol-5-yl]sulfanyl-propan-2-ol

HRID 1988805

Reaktionsgleichung

Reaktionsgleichung von HRID 1988805
[C:1]1([N:11]2[C:15](=[S:16])[N:14]=[N:13][NH:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH:25]1[O:27][CH2:26]1.CCN(CC)CC>CO>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH:25]([OH:27])[CH2:26][S:16][C:15]1[N:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:12]=[N:13][N:14]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27317011,2-Dihydro-1-naphthyl-5H-tetrazole-5-thioneHCID 123223492-(2-Chlorobenzyl)oxirane

Produkt 1

HCID 52751261-(2-Chlorophenyl)-3-[1-(1-naphthyl)tetrazol-5-yl]sulfanyl-propan-2-olAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1,2-dihydro-1-(1-naphthalenyl)-5H-tetrazole-5-thione (50.0 mg, 0.22 mmol), 2-chloro-1-(2,3-epoxypropyl)benzene (36.9 mg, 0.22 mmol) and Et3N (0.15 mL, 1.10 mmol) in MeOH (5 mL) was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by HPLC using a gradient of MeCN/H2O containing TFA (0.1%) (CombiPrep ODS-AQ 50×20 mm, 5μ, 120 Å). The pure fractions were concentrated to give the title compound (12 mg, 14% yield) as a colorless solid.

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by HPLC
  4. additioncontaining TFA (0.1%) (CombiPrep ODS-AQ 50×20 mm, 5μ, 120 Å)
  5. concentrationThe pure fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-85240ee15cd24fff8522dd9ff14ce685
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642277B2

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