creatinine → 1-(5-Methoxy-2-thienyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea

HRID 904170

Reaction equation

[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[CH3:9][O:10][C:11]1[S:15][C:14]([N:16]=[C:17]=[O:18])=[CH:13][CH:12]=1.O>CN(C=O)C.C1(C)C=CC=CC=1>[CH3:9][O:10][C:11]1[S:15][C:14]([NH:16][C:17]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:18])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred suspension of 3.0 g (26 mM) of creatinine in 25 ml of anhydrous DMF was added a solution of 4.1 g (26 mM) of 5-methoxy-2-thienyl isocyanate in 20 ml of toluene. The resulting mixture was heated at 65° C. for 4.5 hrs., cooled, and poured into 200 ml of water. The mixture was extracted with ethyl acetate, and the combined extracts dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate and then ethanol. Final purification was accomplished by chromatography over silica gel (ethyl acetate as eluant), decolorizing the product with charcoal, concentration and recrystallization from acetone-hexane to give 0.23 g of the above urea as a light brown solid, m.p. 180°-182° C. (dec.).

Workup

temperature, cooled
extractionThe mixture was extracted with ethyl acetate
dry with materialthe combined extracts dried (MgSO4)
concentrationconcentrated
customThe residue was recrystallized from ethyl acetate
customFinal purification
concentrationwith charcoal, concentration and recrystallization from acetone-hexane

Sources & evidence

ORD record: ord-727cc847b9654cd5a34f73a1a58857fc
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230713

Linked notes

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