p-Toluenesulfonic acid → HCID 18425436, Verbindung

HRID 1280552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280552
[CH3:1][NH:2][C:3]1[C:8]([CH:9]=S)=[CH:7][N:6]=[C:5](C)[N:4]=1.[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:14]=1[NH2:15].C1(C)C=C[C:24]([S:27](O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:14]=1[NH:15][CH2:9][C:8]1[C:3]([NH:2][CH3:1])=[N:4][C:5]([S:27][CH3:24])=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 118462,6-DichloroanilineHCID 4311764Sodium borohydrideHCID 865928692-Methyl-4-(methylamino)pyrimidine-5-carbothialdehyde

Produkt 1

HCID 18425436HCID 18425436, VerbindungAusbeute 298 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde (6 g, 32.8 mmol), 2,6-dichloroaniline (5.5 g, 33.9 mmol) and 4-toluene-sulfonic acid (1 g, 5.3 mmol) in 70 mL of toluene was heated under reflux with azeotropic removal of water for 17 hours. The mixture was concentrated to a volume of about 10 mL under reduced pressure and then treated with 120 mL of ethanol. The suspension obtained was heated to 75° C. and treated over a period of 15 minutes with 6.2 g (160 mmol) of sodium borohydride pellets. The mixture was stirred for a further 15 minutes and cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was stirred in a mixture of 200 mL of 2M sodium hydroxide solution and 200 mL of ethyl acetate for 1 hour. The phases were separated and the organic phase was dried over magnesium sulfate and filtered. Evaporation of the filtrate under reduced pressure and flash chromatography of the residue using 3:7 diethyl ether/hexane for the elution gave 5.2 g (48%) of 5-(2,6-dichlorophenyl)aminomethyl-4-methylamino-2-methylthio-pyrimidine as a white solid.

Aufarbeitung

  1. temperaturewas heated
  2. concentrationThe mixture was concentrated to a volume of about 10 mL under reduced pressure
  3. additiontreated with 120 mL of ethanol
  4. customThe suspension obtained
  5. temperaturecooled to room temperature
  6. customThe solvent was evaporated under reduced pressure
  7. stirringthe residue was stirred in a mixture of 200 mL of 2M sodium hydroxide solution and 200 mL of ethyl acetate for 1 hour
  8. customThe phases were separated
  9. dry with materialthe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. customEvaporation of the filtrate under reduced pressure and flash chromatography of the residue
  12. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-af3f1183d80e4ac0801c178266ad1aaa
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451804B1

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