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

HRID 904169

Reaction equation

HRID 904169 reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[Br:9][C:10]1[S:14][C:13]([N:15]=[C:16]=[O:17])=[CH:12][CH:11]=1.O>CN(C=O)C.C1(C)C=CC=CC=1>[Br:9][C:10]1[S:14][C:13]([NH:15][C:16]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 588creatinineHCID 962WaterHCID 233337742-Bromo-5-isocyanatothiophene

Product 1

HCID 1359973341-(5-Bromo-2-thienyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) ureaYield 29.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred suspension of 3.0 g (26 mM) of creatinine in 30 ml of anhydrous DMF was added a solution of 5.0 g (26.5 mM) of 5-bromo-2-thienyl isocyanate in 15 ml of toluene. The resulting mixture was heated at 75° C. for 3 hrs., cooled, and poured into 200 ml of water. The precipitate was collected, washed with ethanol and ether, and air-dried. The solid was dissolved in 250 ml hot acetone, treated with charcoal, filtered, and the filtrate diluted with water (250 ml). The resulting precipitate was collected, washed with acetone and then ether. Air-drying gave 2.3 g of the above urea as a buff powder, m.p. 192°-193° C. (dec.).

Workup

  1. temperature, cooled
  2. customThe precipitate was collected
  3. washwashed with ethanol and ether
  4. customair-dried
  5. dissolutionThe solid was dissolved in 250 ml hot acetone
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. additionthe filtrate diluted with water (250 ml)
  9. customThe resulting precipitate was collected
  10. washwashed with acetone
  11. customAir-drying

Sources & evidence

ORD record
ord-fbcc51154ef34c1090a8298350c4eede
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Linked notes

Loading…