Sodium hydride → 2-(3,5-Di-tert-butylbenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazol

HRID 1416227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416227
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([S:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][N:8]=1.[C:17]([C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]=1)[C:24](O)=[O:25])([CH3:20])([CH3:19])[CH3:18].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[C:30]([C:28]1[CH:27]=[C:23]([CH:22]=[C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:29]=1)[C:24]([NH:3][C:4]1[S:5][C:6]([S:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][N:8]=1)=[O:25])([CH3:33])([CH3:32])[CH3:31]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 853393,5-Bis(tert-butyl)benzoic acidHCID 3145445-{[2-(Diethylamino)ethyl]sulfanyl}-1,3,4-thiadiazol-2-amine

Produkt 1

HCID 154109112-(3,5-Di-tert-butylbenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazolAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (0.6 g) and 2-amino-5-diethylaminoethylthio-1,3,4-thiadiazole (2.3 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes while being cooled with ice. 3,5-Di-tert-butylbenzoic acid (2.3 g) and carbonyldiimidazole (1.8 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes at room temperature and the mixture was added to the former reaction mixture. The mixture was stirred for 4 hours at room temperature, and then concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1). The resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 1.5 g of the aimed compound.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. additionthe mixture was added to the former reaction mixture
  3. concentrationconcentrated under a vacuum
  4. additionThe residue, with water added
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe extract was dried over sodium sulfate anhydride
  7. concentrationconcentrated under a vacuum
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  9. customThe resulting solid was recrystallized from n-hexane/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b3c75e11a562440783386f1af1905404
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912258

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