Hydrochloric Acid → N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine

HRID 1866462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866462
COC[O:4][C:5]1[CH:6]=[C:7](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:8]=[CH:9][C:10]=1[O:11]COC.O.Cl.[O-]S([O-])(=O)=O.[Ca+2]>CO.C(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:8]=[CH:9][C:10]=1[OH:11]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24497Calcium SulfateHCID 68977146N-(4-[2-(3,4-di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl}morpholine

Produkt 1

HCID 57978479N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N{4-[2-(3,4-Di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl} morpholine (0.6 g, 1.3347 mmol) was dissolved in a mixed solvent of MeOH (100 mL) and CH2Cl2 (60 mL). The homogeneous solution was bubbled with argon gas. Water (0.2 g, 11.11 mmol) and concentrated hydrochloric acid (0.9 mL, 10.8 mmol) were added and stirred for 45 hours. The solvents were removed by evaporation and the solid residue was washed with water for several times. The solid was dried under high vacuum in the presence of Drierite providing 0.4388 g of N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine as a yellowish solid (1.214 mmol, yield 91.0%). 1H NMR (Acetone-D6 and DMSO-d6, 300.16 MHz) δ (ppm) 9.05 & 9.03 (2s, 0.64H), 8.81 & 8.79 (2s, 0.65H), 7.81 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.3 Hz, 2H), 7.32 (d, J=16.3 Hz, 1H), 7.13-7.04 (m, 2H), 6.96 (dd, J=8.2 & 1.9 Hz, 1H), 6.80 (d, J=8.3 Hz, 1H), 3.68-3.65 (m, 4H) and 2.94-2.91 (m, 4H). MS (ESI) m/z: 362 (M+1)+, 384 (M+23)+ and 745 (2M+23)+.

Aufarbeitung

  1. customThe homogeneous solution was bubbled with argon gas
  2. customThe solvents were removed by evaporation
  3. washthe solid residue was washed with water for several times

Quellen und Nachweise

ORD-Eintrag
ord-6043e73754db4eaf9bbf73fcc72aa94f
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629375B2

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