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

HRID 551237Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-f90eaa8af99c495393e006238c018a69
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947700B2

Reaction notes

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