Hydrochloric Acid → Methyl 4-(4,4-dimethyl-2-oxo-imidazolidin-1-yl)-3-methyl-benzoate

HRID 551237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551237
[CH3:1][C:2]([NH:6][C:7](=[O:20])[NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH3:19])([CH3:5])[CH2:3]O.[K].CC(C)([O-])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C1COCC1.O>[CH3:1][C:2]1([CH3:5])[CH2:3][N:8]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[CH3:19])[C:7](=[O:20])[NH:6]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 50987170Potassium tertbutoxideHCID 67048374Methyl 4-(3-[1,1-dimethyl-2-hydroxy-ethyl]ureido)-3-methyl-benzoate

Produkt 1

HCID 67048320Methyl 4-(4,4-dimethyl-2-oxo-imidazolidin-1-yl)-3-methyl-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

7.00 g (25.0 mmol) methyl 4-(3-[1,1-dimethyl-2-hydroxy-ethyl]-ureido)-3-methyl-benzoate are dissolved in 400 ml THF at 0° C. and combined with 6.73 g (60.0 mmol) potassium-tert.-butoxide. After stirring for 15 minutes at 0° C. a solution of 5.72 g (30.0 mmol) p-toluenesulphonic acid in 50 ml THF is added dropwise. After another 10 minutes stirring at 0° C. 300 ml of water are added, the mixture is neutralised with 1-molar hydrochloric acid and the THF is removed i. vac. The residue is extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated down i. vac. Then the residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol=100:0->97:3).

Aufarbeitung

  1. additionis added dropwise
  2. customthe THF is removed i
  3. extractionThe residue is extracted with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated down i
  6. customThen the residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol=100:0->97:3)

Quellen und Nachweise

ORD-Eintrag
ord-f90eaa8af99c495393e006238c018a69
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947700B2

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