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Triphenylphosphine → 3-Methyl-5-[3-[4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazole

HRID 2400113
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2400113
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][N:8]=[C:7]([CH3:10])[N:6]=1.[F:11][CH:12]([F:27])[C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[C:22]([CH3:24])[C:21](O)=[C:20]([CH3:26])[CH:19]=2)[N:14]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:10][C:7]1[N:6]=[C:5]([CH2:4][CH2:3][CH2:2][O:1][C:21]2[C:20]([CH3:26])=[CH:19][C:18]([C:15]3[N:14]=[C:13]([CH:12]([F:11])[F:27])[O:17][N:16]=3)=[CH:23][C:22]=2[CH3:24])[S:9][N:8]=1
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 189678815-(3-Hydroxypropyl)-3-methyl-1,2,4-thiadiazoleHCID 1355842214-(5-Difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol

Produkt 1

HCID 189678883-Methyl-5-[3-[4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazole
Ausbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 5-(3-hydroxypropyl)-3-methyl-1,2,4-thiadiazole (242 mg, 1.53 mmol), 4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol described in allowed U.S. patent application Ser. No. 07/869,287, incorporated herein by reference (400 mg, 1.67 mmol), and DEAD (290 mg, 1.67 mmol) was dissolved in 16 mL of THF. To the above solution was added triphenylphosphine (438 mg, 1.67 mmol) at 0° C. and the mixture was allowed to warm to 20° C. overnight. The solvent was removed in vacuo, an aqueous sodium bicarbonate solution was added, and the mixture was extracted with methylene chloride (7×). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, from 1/6 to 1/4) followed by recrystallization from ethyl acetate/hexane to afford 471 mg (81%) of 3-methyl-5-[3-[4-(5-difluoromethyl-1,2,4-oxadiazol-3 -yl)-2,6-dimethylphenoxy]propyl]-1,2,4thiadiazole, as a white crystalline solid, m.p. 62°-64° C.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionan aqueous sodium bicarbonate solution was added
  3. extractionthe mixture was extracted with methylene chloride (7×)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, from 1/6 to 1/4)
  7. customfollowed by recrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4469656661894147b8913c3a45875625
Quelldatensatz
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05453433

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