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Water → 2-[6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

HRID 477594
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Reaktionsgleichung

Reaktionsgleichung von HRID 477594
[NH2:1][C:2]1[C:3]([F:15])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]#[CH:13])[C:6]=2[CH:14]=1.[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2[CH2:22][CH2:23][CH2:24][CH2:25][C:17]1=2.O>C(O)(=O)C>[F:15][C:3]1[C:2]([N:1]2[C:19](=[O:20])[C:18]3[CH2:22][CH2:23][CH2:24][CH2:25][C:17]=3[C:16]2=[O:21])=[CH:14][C:6]2[N:7]([CH2:11][C:12]#[CH:13])[C:8](=[O:10])[S:9][C:5]=2[CH:4]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 139609955-Amino-6-fluoro-3-(prop-2-yn-1-yl)-1,3-benzothiazol-2(3H)-one

Produkt 1

HCID 140139642-[6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dioneAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

5-Amino-6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolone (0.43 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.32 g) were suspended in acetic acid (5 ml), and the resultant suspension was heated under reflux for 5 hours. After being allowed to cool, water was added thereto, and the resultant mixture was extracted with ethyl acetate. The extract was washed with water and an aqueous sodium bicarbonate solution, dried and concentrated. The residue was purified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:4) to give 2-[6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.13 g). m.p., 193°-195° C. Recrystallization from 2-propanol gave the purified product. m.p., 198°-199° C.

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. temperatureto cool
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialan aqueous sodium bicarbonate solution, dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-e1e24f49ed2d41fc89f78ca05af436fc
Quelldatensatz
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04888428

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