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Diisopropylamine → N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea

HRID 974054
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 974054
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:31]([F:41])[CH:30]=2)[CH3:28])[N:26]=1.[CH3:42][N:43]=[C:44]=[S:45]>O1CCCC1>[CH3:42][NH:43][C:44]([NH:21][C:22]1[S:23][CH:24]=[C:25]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[C:31]([F:41])[CH:30]=2)[CH3:28])[N:26]=1)=[S:45]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 7912DiisopropylamineHCID 11167Methyl isothiocyanateHCID 2724682Lithium diisopropylamideHCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleHCID 178418339Butyllithium

Produkt 1

HCID 15676068N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea
Ausbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To lithium diisopropylamide in tetrahydrofuran prepared with diisopropylamine (0.187 g, 1.85 mmol) and n-butyllithium (1.9 mmol) was added 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (0.50 g, 1.68 mmol) in tetrahydrofuran at -70° C. After the mixture was stirred for 20 min, methylisothiocyanate (0.131 g, 1.8 mmol) in tetrahydrofuran was added to the mixture. After the mixture was stirred at room temperature for 3.5 h, the mixture was evaporated under reduced pressure to a residue, which was extracted with chloroform. The extracts were washed with water, dried over, and evaporated under reduced pressure to a residue, which was chromatographed and recrystallized to afford N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea (0.233 g, 35% yield) as crystalline material: mp 180.5°-181.0° C.

Aufarbeitung

  1. stirringAfter the mixture was stirred at room temperature for 3.5 h
  2. customthe mixture was evaporated under reduced pressure to a residue, which
  3. extractionwas extracted with chloroform
  4. washThe extracts were washed with water
  5. customdried over, and
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed
  8. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-5a9e03d33fb94f99a0834fbff72218cf
Quelldatensatz
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05066666

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