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

HRID 904166

Reaction equation

HRID 904166 reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[Cl:9][C:10]1[CH:11]=[C:12]([N:15]=[C:16]=[O:17])[S:13][CH:14]=1.O>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]([NH:15][C:16]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:17])[S:13][CH:14]=1

Participants

6

Reactant 3

HCID 588creatinineHCID 962WaterHCID 233337774-Chloro-2-thienyl isocyanate

Product 1

HCID 1361239481-(4-Chloro-2-thienyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To 3.0 g (26.5 mM) of creatinine in 50 ml of anhydrous DMF was added with stirring a solution of 4-chloro-2-thienyl isocyanate in 25 ml of toluene. After stirring at 65° C. for 5 hrs., the mixture was cooled, added to 200 ml of water and filtered to separate a precipitate, which was recrystallized from ethanol and then ethyl acetate to give 1.0 g of the above urea as a light tan solid, m.p. 203°-204° C. (dec.) containing 1/8 mole of ethyl acetate of recrystallization.

Workup

  1. temperature, the mixture was cooled
  2. filtrationfiltered
  3. customto separate a precipitate, which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-a4b67dcb19ad48c8a85899e8036a6441
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Linked notes

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