Thionyl Chloride → 4-(N,N-Dimethylsulfamoyl)-3-methoxybenzyl chloride

HRID 11895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11895
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]O)=[CH:8][C:7]=1[O:14][CH3:15])(=[O:5])=[O:4].S(Cl)([Cl:19])=O>C(Cl)Cl>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][Cl:19])=[CH:8][C:7]=1[O:14][CH3:15])(=[O:5])=[O:4]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 685585254-(N,N-Dimethylsulfamoyl)-3-methoxybenzyl alcohol

Produkt 1

HCID 219768424-(N,N-Dimethylsulfamoyl)-3-methoxybenzyl chlorideAusbeute 104,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of OBS02014 (2.76 g, 10.55 mmol) in anhydrous DCM (50 mL) was added thionyl chloride (1.15 mL, 15.82 mmol). The mixture was stirred at room temperature for 2 h and the volatiles removed in vacuo. The residue was re-dissolved and co-evaporated three times with DCM (3×20 mL) to give OBS02016 as a brown oil (2.91 g, 99%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.84; 1H-NMR (270 MHz, CDCl3)=2.96 (6H, s), 3.90 (3H, s), 4.55 (2H, s), 6.95 (1H, dd, J=1.8, 8.0), 7.01 (1H, d, J=1.8), 7.32 (1H, d, J=8.0). Dimethylsulfamic Acid 4-{[(4-cyano-phenyl)-[1,2,4]triazol-4-ylamino]methyl}-2-methoxyphenyl ester (OBS02017, STX739)

Aufarbeitung

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residue was re-dissolved

Quellen und Nachweise

ORD-Eintrag
ord-19c47b15572e4f0d927f5edbf6903370
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098343B2

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