Oxalyl chloride → 2-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide

HRID 1753720

Reaktionsgleichung

Reaktionsgleichung von HRID 1753720
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1.[CH3:8][O:9][C:10]1[C:18]([S:19][CH3:20])=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[CH3:8][O:9][C:10]1[C:18]([S:19][CH3:20])=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=[CH:15][C:11]=1[C:12]([NH:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1)=[O:13]

Komponenten

5

Edukt 3

HCID 65578Oxalyl chloride2×HCID 1384921-methyl-1H-tetrazol-5-amineHCID 669579072-Methoxy-3-methylthio-4-(trifluoromethyl)benzoic acid

Produkt 1

HCID 897687922-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamideAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1.45 g (98% by weight; 14.3 mmol) of 5-amino-1-methyl-1H-tetrazole were added to 3.00 g (11.3 mmol) of 2-methoxy-3-(methylsulfanyl)-4-(trifluoromethyl)benzoic acid in 30 ml of dry pyridine. 2.00 g (15.8 mmol) of oxalyl chloride were then added, and the mixture was subsequently stirred at room temperature (RT) for three days. Another 500 mg (3.94 mmol) of oxalyl chloride were then added, and the mixture was subsequently stirred at RT for 16 h. For work-up, the contents were substantially freed from the solvent on a rotary evaporator. The residue was stirred with dichloromethane and a saturated solution of sodium bicarbonate. The organic phases were then separated and the organic phase was freed from the solvent on a rotary evaporator. The residue was purified chromatographically, which gave 1.83 g of clean product.

Aufarbeitung

  1. stirringthe mixture was subsequently stirred at RT for 16 h
  2. customFor work-up, the contents were substantially freed from the solvent on a rotary evaporator
  3. stirringThe residue was stirred with dichloromethane
  4. customThe organic phases were then separated
  5. customthe organic phase was freed from the solvent on a rotary evaporator
  6. customThe residue was purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-6e42f933ffe44b92a03fe1941df17cc5
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09167819B2

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