Trichloroacetyl chloride → 2,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide

HRID 1441460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441460
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)=[O:19].[Cl:27][C:28]([Cl:33])([Cl:32])[C:29](Cl)=[O:30].C(N(CC)CC)C>C(Cl)Cl>[Cl:27][C:28]([Cl:33])([Cl:32])[C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18](=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)=[O:30]

Komponenten

5

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 17976112[2-Amino-5(4-methoxybenzoyl)phenyl](3-chlorophenyl)-methanone

Produkt 1

HCID 179760992,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A mixture of intermediate 11 (0.0536 mol) in DCM (200 ml) was cooled to 5° C. under N2 flow. A solution of trichloro-acetylchloride (0.0643 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 30 minutes. A solution of triethylamine (0.0643 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour then at room temperature for 2 hours, poured out into ice water and extracted with DCM. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated, yielding 27.4 g (quantitative) of 2,2,2-trichloro- N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide (intermediate 12).

Aufarbeitung

  1. stirringThe mixture was stirred at 5° C. for 1 hour
  2. waitat room temperature for 2 hours
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b33bb09e87394f83ad3da2cd54935e27
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655654B2

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