Tert-Butylamine → N-t-Butyl-4-chloro-2-fluorobenzamide

HRID 1934345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934345
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.O>[C:12]([NH:16][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[F:11])([CH3:15])([CH3:14])[CH3:13]

Komponenten

7

Edukt 4

HCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 991524-Chloro-2-fluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 10130797N-t-Butyl-4-chloro-2-fluorobenzamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 4-chloro-2-fluorobenzoic acid (0.3494 g, 2.00 mmol) in methylene chloride (10 ml) were added t-butyl amine (0.32 ml, 3.05 mmol) and HOBt (0.3248 g, 2.40 mmol), and then WSC HCl (0.4596 g, 2.40 mmol) was added and stirred for 3 hours. The reaction mixture was added into water and extracted three times with ethyl acetate. The combined extracts were dried over MgSO4. The solvent was evaporated and the residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1) to give the title compound (0.4403 g; 96%).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined extracts were dried over MgSO4
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-2bf48e9da07f4048b6def2bef758f499
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384033B1

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