Thionyl Chloride → n-(3,5-Bis trifluoromethyl-benzyl)-n-cyclopropyl-4-o-tolyl-nicotinamide

HRID 1017428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017428
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[F:21][C:22]([F:39])([F:38])[C:23]1[CH:24]=[C:25]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:26][NH:27][CH:28]1[CH2:30][CH2:29]1>ClCCl.CN(C)C=O>[F:21][C:22]([F:38])([F:39])[C:23]1[CH:24]=[C:25]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=1)[CH2:26][N:27]([CH:28]1[CH2:29][CH2:30]1)[C:13](=[O:15])[C:12]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:16])=[CH:8][CH:9]=[N:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 158874064-(2-Methylphenyl)nicotinic acidHCID 15887407(3,5-Bistrifluoromethylbenzyl)cyclopropylamine

Produkt 1

HCID 9806536n-(3,5-Bis trifluoromethyl-benzyl)-n-cyclopropyl-4-o-tolyl-nicotinamideAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 106 mg (0.5 mmol) 4-o-tolyl-nicotinic acid in 5 ml dichloromethane and 2 drops N,N-dimethylformamide was stirred with 0.1 ml (1.4 mmol) thionyl chloride for 1.5 h at room temperature. The solvent was removed and the residue was taken up in 5 ml dichloromethane and 0.3 ml triethylamine. After the addition of 155 mg (0.55 mmol) (3,5-bis-trifluoromethyl-benzyl)-cyclopropyl-amine the mixture was stirred at room temperature for 1 h and washed twice with water. The organic layer was dried (magnesium sulfate) and evaporated. The crude oil was subjected to column chromatography to give 140 mg (58%) of the title compound as an oil.

Aufarbeitung

  1. customThe solvent was removed
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b81ce9eeca524e38991e6f35bf2495e1
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479483B2

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