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Triethylamine → HCID 58531629, Verbindung

HRID 1889655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1889655
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[C:19]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)#[N:20].CCN(CC)CC.S(Cl)(Cl)(=O)=O>C1COCC1>[C:19]([C:21]1[CH:22]=[C:23]([S:27]([N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:17]=[C:16]([Cl:18])[CH:15]=2)[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)#[N:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 24648Sulfuryl chlorideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 58531427N-(3,5-Dichlorobenzyl)-1-(4-fluorophenyl)methanamine

Produkt 1

HCID 58531629HCID 58531629, VerbindungAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of N-(3,5-dichlorobenzyl)-1-(4-fluorophenyl)methanamine (1.40 g, 4.91 mmol) in THF (15 mL) was added 3-cyanobenzene-1-sulfonyl chloride (0.9 g, 4.46 mmol) and Et3N (1.22 mL, 8.93 mmol) at rt for 2 h. Additional sulfonyl chloride (0.35 g) and Et3N (0.5 mL) were added. The reaction mixture was stirred at rt for 15 h. The mixture was concentrated and the residue was diluted with ethyl acetate and 1 N HCl solution. The organic layer was separated, washed with brine, saturated aq NaHCO3 solution, dried over MgSO4, and concentrated to give a glassy material which was purified by flash silica gel column chromatography on silica gel (ISCO. Column: 24 g. Eluent: A: hexane. B: ethyl acetate. Condition: A to 25% of B (50 min gradient) to obtain the desired product as a white solid (1.8 g, 81%). 1H NMR (CDCl3): δ 8.08-8.02 (m, 2H), 7.93-7.90 (m, 1H), 7.70 (t, J=8.0 Hz, 1H), 7.25-7.24 (m, 1H), 7.13-7.09 (m, 2H), 6.98 (t, J=8.0 Hz, 2H), 6.90 (d, J=4.0 Hz, 2H), 4.38 (s, 2H), 4.30 (s, 2H); MS (ESI): [M−H]−=506.9.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate and 1 N HCl solution
  3. customThe organic layer was separated
  4. washwashed with brine, saturated aq NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a glassy material which
  8. customwas purified by flash silica gel column chromatography on silica gel (ISCO

Quellen und Nachweise

ORD-Eintrag
ord-cdda134614a44fad8e4c0629a105e865
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501992B2

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