Cyanamide → HCID 89766894, Verbindung

HRID 1749133

Reaktionsgleichung

Reaktionsgleichung von HRID 1749133
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[C:17]([S:18][CH3:19])=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[N:24]#[C:25][NH2:26].BrN1C(=[O:33])CCC1=O.O.[Mn]([O-])(=O)(=O)=O.[Na+].S(=O)(=O)(O)[O-].[Na+]>CO>[C:25]([N:26]=[S:18]([C:17]1[C:9]([O:8][CH3:7])=[C:10]([CH:14]=[CH:15][C:16]=1[C:20]([F:23])([F:22])[F:21])[C:11]([OH:13])=[O:12])([CH3:19])=[O:33])#[N:24]

Komponenten

8

Edukt 6

HCID 9864CyanamideHCID 67184N-bromobutanimideHCID 516876Sodium permanganate monohydrate2×HCID 516919Sodium BisulfateHCID 23665647Potassium tert-butoxideHCID 669579072-Methoxy-3-methylthio-4-(trifluoromethyl)benzoic acid

Produkt 1

HCID 89766894HCID 89766894, VerbindungAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3.71 g (33.1 mmol) of potassium tert-butoxide were added to a solution of 4.00 g (15.0 mmol) of 2-methoxy-3-(methylsulfanyl)-4-(trifluoromethyl)benzoic acid in 250 ml of methanol. The mixture was stirred for 10 minutes, and 1.07 g (25.5 mmol) of cyanamide and 4.81 g (27.0 mmol) of N-bromsuccinimide were then added in succession. The contents was then stirred at RT for 2 h. The mixture was then freed from the solvent on a rotary evaporator and the residue was taken up in a mixture of in each case 120 ml of acetonitrile and water. 7.21 g (45.1 mmol) of sodium permanganate monohydrate were added, and the mixture was stirred at RT for one week. During this week, both after one day and after a further day, in each case 3.6 g (22.5 mmol) of sodium permanganate monohydrate were added. For work-up, a 10% by weight strength solution of sodium bisulfate was added. On a rotary evaporator, at a temperature of at most 30° C., the solvent was substantially removed. The residue was cooled in an ice bath and then acidified with 1 M hydrochloric acid. The mixture was extracted three times with ice-cold dichloromethane. The combined organic phases were freed from the solvent on a rotary evaporator and the residue was purified chromatographically, which gave 1.30 g of product of a purity of 80% by weight.

Aufarbeitung

  1. stirringThe contents was then stirred at RT for 2 h
  2. customThe mixture was then freed from the solvent on a rotary evaporator
  3. additionthe residue was taken up in a mixture of in each case 120 ml of acetonitrile and water
  4. stirringthe mixture was stirred at RT for one week
  5. waitDuring this week
  6. waitafter one day
  7. waitafter a further day
  8. customOn a rotary evaporator
  9. customat a temperature of at most 30° C., the solvent was substantially removed
  10. temperatureThe residue was cooled in an ice bath
  11. extractionThe mixture was extracted three times with ice-cold dichloromethane
  12. customThe combined organic phases were freed from the solvent on a rotary evaporator
  13. customthe residue was purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-2a057b4de2ea43eda1a10a675afbdfb3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156784B2

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