Thionyl Chloride → HCID 23295002, Verbindung

HRID 1955265

Reaktionsgleichung

Reaktionsgleichung von HRID 1955265
[C:1]1([C:7]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:16].[CH:18]([N:21]([CH:25](O)[CH3:26])[CH:22](C)[CH3:23])(C)[CH3:19]>>[ClH:16].[C:1]1([C:7]2([C:11]([O:13][CH2:19][CH2:18][N:21]([CH2:25][CH3:26])[CH2:22][CH3:23])=[O:12])[CH2:8][CH2:9][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 3

HCID 24386Thionyl ChlorideHCID 2771711-Phenylcyclobutanecarboxylic acidHCID 22348659HCID 22348659, Verbindung

Produkt 1

HCID 23295002HCID 23295002, Verbindung

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-Phenylcyclobutanecarboxylic acid (1.9 mmol) was refluxed with SOCl2 (5 mL). After 0.5 h, the reaction mixture was evaporated and the residue dissolved in toluene. Diisopropylaminoethanol (3.8 mmol) was added and the mixture was heated at 80° C. for 1.5 h. The reaction mixture was filtered and chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 1.3 g (73%); mp 137-139° C.; 1H NMR (D2O) δ 1.25 (t, 6H), 1.92-2.01 (m, 1H), 2.07-2.16 (m, 1H), 2.64 (m, 2H), 2.89 (m, 2H), 3.11 (q, 4H), 3.50 (t, 2H), 4.48 (t, 2H), 7.44 (m, 1H), 7.48 (m, 2H), 7.53 (m, 2H). Anal. (C17H25NO2.HCl) C, H, N.

Aufarbeitung

  1. customthe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in toluene
  3. filtrationThe reaction mixture was filtered
  4. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-18f4d0e48b7145678c6c6cd10f086ed9
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124354

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