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Formaldehyde → 3-(3,5-Dichloro-4-methoxybenzoyl)-5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole

HRID 385161
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 385161
Cl.NC1C=C(C(F)(F)F)C=CC=1S.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[CH:18][C:19]2[S:23][CH2:22][NH:21][C:20]=2[CH:24]=1.C=O.[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([Cl:41])[C:38]=1[O:39][CH3:40])[C:33](Cl)=[O:34]>ClCCl.O.C(N(CC)CC)C>[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([Cl:41])[C:38]=1[O:39][CH3:40])[C:33]([N:21]1[C:20]2[CH:24]=[C:16]([C:15]([F:14])([F:25])[F:26])[CH:17]=[CH:18][C:19]=2[S:23][CH2:22]1)=[O:34]
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Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochlorideHCID 38303153,5-Dichloro-4-methoxybenzoyl chlorideHCID 218361675-Trifluoromethyl-2,3-dihydro-1,3-benzothiazole

Produkt 1

HCID 681090693-(3,5-Dichloro-4-methoxybenzoyl)-5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

2-amino-4-trifluoromethylbenzenethiol hydrochloride (502 mg), and 5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole synthesized from 37% formalin (0.18 mL) and triethylamine (0.30 mL) in the same manner as in Example 38 were dissolved in dichloromethane (5 mL), and triethylamine (0.30 mL) and 3,5-dichloro-4-methoxybenzoyl chloride (354 mg) were added to the solution, and then the mixture was stirred at room temperature for 2 hours. Water was added and 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=8:1) to obtain the title compound (223 mg) as a colorless oily substance.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-d5012945561b40dab83d8844f581d420
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367843B2

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