Formaldehyde → 3-(3-Formyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

HRID 385125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385125
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH2:2]1.NC1C=CC=CC=1S.C=O.C(N(C(C)C)CC)(C)C.[CH:29]([C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([C:42]([F:45])([F:44])[F:43])[C:39]=1[O:40][CH3:41])[C:34](Cl)=[O:35])=[O:30]>ClCCl>[CH:29]([C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([C:42]([F:43])([F:45])[F:44])[C:39]=1[O:40][CH3:41])[C:34]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:35])=[O:30]

Komponenten

7

Edukt 5

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 81531DiisopropylethylamineHCID 96588BenzothiazolineHCID 866681783-Formyl-4-methoxy-5-trifluoromethylbenzoyl chloride

Produkt 1

HCID 866681793-(3-Formyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (1.55 g) and 37% formalin (1.0 mL) in the same manner as in Example 1 was dissolved in dichloromethane (15 mL), and diisopropylethylamine (2.7 mL) and 3-formyl-4-methoxy-5-trifluoromethylbenzoyl chloride (2.42 g) were added to the solution, and then the mixture was stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (1.44 g) as a yellow oily substance.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-8ff2c5cde9514b808845ff208181ecd4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367843B2

Notizen zur Reaktion

Wird geladen…