Formaldehyde → 3-(3-Cyano-5-isopropyl-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole

HRID 385043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385043
[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:20]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26])#[N:21]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:30]=1[O:31][CH3:32])[C:25]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:26])#[N:21]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 96588BenzothiazolineHCID 866681543-Cyano-5-isopropyl-4-methoxybenzoyl chloride

Produkt 1

HCID 681079533-(3-Cyano-5-isopropyl-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (1.25 g) and 37% formalin (0.83 mL) in the same manner as in Example 1 was dissolved in chloroform (7 mL), and triethylamine (1.25 mL) and 3-cyano-5-isopropyl-4-methoxybenzoyl chloride (710 mg) were added to the solution, and then the mixture was stirred at room temperature for 2 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=6:1) to obtain the title compound (1.02 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=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-6df25c63774544e0aaba3fae9bde914e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367843B2

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