Cyanamide → HCID 89768781, Verbindung

HRID 1753721

Reaktionsgleichung

Reaktionsgleichung von HRID 1753721
[N:1]#[C:2][NH2:3].BrN1C(=[O:10])CCC1=O.[CH3:12][O:13][C:14]1[C:28]([S:29][CH3:30])=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=[CH:25][C:15]=1[C:16]([NH:18][C:19]1[N:23]([CH3:24])[N:22]=[N:21][N:20]=1)=[O:17].CC(C)([O-])C.[K+].O.[Mn]([O-])(=O)(=O)=O.[Na+].S(=O)(=O)(O)[O-].[Na+]>CO.O>[C:2]([N:3]=[S:29]([C:28]1[C:14]([O:13][CH3:12])=[C:15]([CH:25]=[CH:26][C:27]=1[C:31]([F:32])([F:34])[F:33])[C:16]([NH:18][C:19]1[N:23]([CH3:24])[N:22]=[N:21][N:20]=1)=[O:17])[CH3:30])#[N:1].[C:2]([N:3]=[S:29]([C:28]1[C:14]([O:13][CH3:12])=[C:15]([CH:25]=[CH:26][C:27]=1[C:31]([F:33])([F:34])[F:32])[C:16]([NH:18][C:19]1[N:23]([CH3:24])[N:22]=[N:21][N:20]=1)=[O:17])([CH3:30])=[O:10])#[N:1]

Komponenten

10

Edukt 6

HCID 9864CyanamideHCID 67184N-bromobutanimideHCID 516876Sodium permanganate monohydrateHCID 516919Sodium BisulfateHCID 23665647Potassium tert-butoxideHCID 897687922-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide

Produkt 2

HCID 89768781HCID 89768781, VerbindungHCID 89768782HCID 89768782, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

At RT, 234 mg (5.56 mmol) of cyanamide and 1.06 g (5.96 mmol) of N-bromosuccinimide were added in succession to a solution of 1.14 g (3.27 mmol) of 2-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 440 mg (3.92 mmol) of potassium tert-butoxide in 70 ml of methanol. The contents were then stirred at RT for 16 h. For work-up, the mixture was freed from the solvent on a rotary evaporator at a temperature of at most 30° C. The residue was stirred in a mixture of 150 ml of ice-cold dichloromethane and 50 ml of ice-cold aqueous 10% by weight strength sodium bisulfate solution for about two minutes. After phase separation, the aqueous phase was extracted with 50 ml of dichloromethane. On a rotary evaporator, the combined organic phases were freed from the solvent. The residue was taken up in 60 ml of acetonitrile and 60 ml of water. 1.57 g (9.80 mmol) of sodium permanganate monohydrate were then added. The reaction mixture was stirred at RT for four days. For work-up, aqueous 10% by weight strength sodium bisulfate solution was added. Water was then added, and the mixture was extracted three times with dichloromethane. On a rotary evaporator, the combined organic phases were freed from the solvent at a temperature of at most 30° C. The residue was purified chromatographically, which gave 40 mg of 3-(N-cyano-S-methylsulfinimidoyl)-2-methoxy-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 650 mg of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

Aufarbeitung

  1. customFor work-up, the mixture was freed from the solvent on a rotary evaporator at a temperature of at most 30° C
  2. stirringThe residue was stirred in a mixture of 150 ml of ice-cold dichloromethane and 50 ml of ice-cold aqueous 10% by weight strength sodium bisulfate solution for about two minutes
  3. customAfter phase separation
  4. extractionthe aqueous phase was extracted with 50 ml of dichloromethane
  5. customOn a rotary evaporator
  6. stirringThe reaction mixture was stirred at RT for four days
  7. extractionthe mixture was extracted three times with dichloromethane
  8. customOn a rotary evaporator
  9. customwere freed from the solvent at a temperature of at most 30° C
  10. customThe residue was purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-57f46a2cf8b64ab2908d72254c341c93
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09167819B2

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