4-Isopropylbenzoic Acid → 2-(4-Isopropylbenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazole

HRID 1416222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416222
[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.[CH:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[CH:17]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:3][C:4]2[S:5][C:6]([S:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][N:8]=2)=[O:25])=[CH:27][CH:28]=1)([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 108204-Isopropylbenzoic AcidHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 3145445-{[2-(Diethylamino)ethyl]sulfanyl}-1,3,4-thiadiazol-2-amine

Produkt 1

HCID 99296792-(4-Isopropylbenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazoleAusbeute 94,9 %

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. 4-Isopropylbenzoic acid (1.6 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 3.5 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-f61cda270da34602b94c2c87dcdfe384
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912258

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