Hydrochloric Acid → N-(t-butoxy)-5-(4-chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamide

HRID 1392363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392363
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:57]([O:61][NH2:62])([CH3:60])([CH3:59])[CH3:58].Cl>C(#N)C.C(OCC)(=O)C>[C:57]([O:61][NH:62][C:13]([C:11]1[S:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[N:10]=1)=[O:15])([CH3:60])([CH3:59])[CH3:58]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2777907O-tert-butylhydroxylamineHCID 10045599HCID 10045599, Verbindung

Produkt 1

HCID 86595683N-(t-butoxy)-5-(4-chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Part B; 5-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid (1.00 gram, 2.6 mmol) is suspended in anhydrous acetonitrile (20 mL) under a nitrogen atmosphere at room temperature. Diisopropylethylamine (DIPEA) (1.36 mL, 7.8 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (1.08 gram, 2.85 mmol) and O-tert-butylhydroxylamine.HCl (0.35 gram, 25.1 mmol) are successively added and the resulting mixture is stirred overnight at room temperature. The resulting mixture is concentrated in vacuo and dichloromethane is added. The resulting solution is successively washed with water and brine, dried over MgSO4, filtered and evaporated in vacuo. Subsequent flash chromatography (ethyl acetate:petroleum ether (40-60)=1:3 (v/v)) gives N-(t-butoxy)-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxamide (0.60 gram, 51% yield) as a white foam. 1H-NMR (400 MHz, CDCl3): δ 9.20 (s, 1H), 7.47 (t, J=2 Hz, 1H), 7.25-7. (m, 4H), 7.14 (dt, J=8 Hz, J=2 Hz, 2H), 1.36 (s, 9H).

Aufarbeitung

  1. concentrationThe resulting mixture is concentrated in vacuo and dichloromethane
  2. additionis added
  3. washThe resulting solution is successively washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ad8f21a2cfca437da949bc55155f3dc5
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342032B2

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