Hydrochloric Acid → 4-{3E-[4-Methoxy-2-(2-morpholin 4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzoic acid, hydrochloride

HRID 10680

Reaktionsgleichung

Reaktionsgleichung von HRID 10680
[CH3:1][O:2][C:3]1[C:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][C:6]([CH:7]=O)=[C:5]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:4]=1.[C:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)(=[O:27])[CH3:26].C[O-].[Li+].[ClH:40]>CN(C)C=O.CO.O>[ClH:40].[CH3:1][O:2][C:3]1[C:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][C:6](/[CH:7]=[CH:26]/[C:25]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=2)=[O:27])=[C:5]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:4]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 114704-Acetylbenzoic AcidHCID 4177230Lithium methanolateHCID 161161844-Methoxy-2-(2-morpholin-4-ylethoxy)-5-thien-2-ylbenzaldehyde

Produkt 1

HCID 102395174-{3E-[4-Methoxy-2-(2-morpholin 4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzoic acid, hydrochlorideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21901440N,N-dimethylformamide methanolLösungsmittel

Versuchsvorschrift

4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.15 g, 0.43 mmol) and 4-acetylbenzoic acid (0.071 g, 0.43 mmol) were dissolved in a dimethylformamide-methanol solution (3.0 mL, 7:3). After complete dissolution, lithium methoxide (0.065 g, 1.7 mmol) was added and the resulting bright orange slurry was stirred in the dark at room temperature for 2 h. Upon completion, as determined by HPLC, the mixture was diluted with water (10 mL), acidified with a 1 N hydrochloric acid solution, and extracted with an ethyl acetate:tetrahydrofuran mixture (1:1, 6×20 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude solid was slurried in ethyl alcohol (5 mL) to remove residual impurities and the resulting solid was collected on filter paper and dried in vacuo to yield 0.21 g (98%) of the title compound as a dark yellow solid, mp: 255° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 8.34 (s, 1H), 8.26 (d, 2H, J=8.7 Hz), 8.11 (d, 2H, J=8.7 Hz), 8.08 (s, 1H), 7.95 (d, 1H, J=15.9 Hz), 7.71 (d, 1H, J=3.3 Hz), 7.55 (d, 1H, J=4.5 Hz), 7.15 (dd, 1H, J=4.5, 3.3 Hz), 6.94 (s, 1H), 4.68 (brs, 2H), 4.04 (s, 3H), 3.98 (brs, 2H), 3.81–3.88 (brm, 2H), 3.70 (brs, 2H), 3.54–3.58 (brm, 2H), 3.29 (brs, 2H). MS (ESI) m/z=494 ([M+H]+, 100%). Anal. Calcd. for C27H28ClNO6S: C, 61.18; H, 5.32; Cl, 6.69; N, 2.64; S, 6.05. Found: C, 61.18; H, 5.41; Cl, 6.16; N, 2.73; S, 5.87.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with an ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated to dryness
  5. customto remove residual impurities
  6. customthe resulting solid was collected
  7. filtrationon filter paper
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b7f81d6e4fb24ae099acd0a0c7aec7fd
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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