creatinine → HCID 136074472, compound

HRID 904172Notes

Reaction equation

HRID 904172 reaction equation
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[O:9]1[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[O:16])=[CH:10]1>CN(C=O)C.C1(C)C=CC=CC=1>[O:9]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:16])=[CH:10]1

Participants

5

Reactant 2

HCID 588creatinineHCID 115283353-isocyanatofuran

Product 1

HCID 136074472HCID 136074472, compoundYield 1.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 18.3 g (162 mM) of creatinine in 120 ml of anhydrous DMF was added a solution of 17.2 g (162 mM) of 3-furanyl isocyanate in 80 ml of toluene. After stirring the mixture for 3 hrs. at 65° C., the mixture was partially concentrated under vacuum and the residue poured into 1200 ml of water. The resulting precipitate was collected, washed with water and recrystallized from ethyl acetate. The solid was then chromatographed over silica gel using ethyl acetate as the eluant and the fractions containing the product were concentrated and the residue recrystallized from toluene to give 0.5 g of the above urea as a tan solid, m.p. 179°-181° C. (dec.).

Workup

  1. concentrationat 65° C., the mixture was partially concentrated under vacuum
  2. additionthe residue poured into 1200 ml of water
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customrecrystallized from ethyl acetate
  6. customThe solid was then chromatographed over silica gel
  7. additionthe fractions containing the product
  8. concentrationwere concentrated
  9. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-32fcc878990c42e8b5fbc377663e90f6
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Reaction notes

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