creatinine → HCID 136174789, compound

HRID 904171Notes

Reaction equation

HRID 904171 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][CH:11]=[C:10]1[N:14]=[C:15]=[O:16]>CN(C=O)C.C1(C)C=CC=CC=1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[NH:14][C:15]([N:8]=[C:7]1[NH:6][C:4](=[O:5])[CH2:3][N:2]1[CH3:1])=[O:16]

Participants

5

Reactant 2

HCID 588creatinineHCID 11286446Furan, 2-isocyanato-

Product 1

HCID 136174789HCID 136174789, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 6.9 g (60 mM) of creatinine in 100 ml of anhydrous DMF was added a solution of 6.5 g (60 mM) of 2-furanyl isocyanate in 75 ml of toluene. After stirring the mixture 1 hr. at 25° C. and then 1 hr. at 55° C., the solvents were removed in vacuo and the residue taken up in ethyl acetate and washed with water. The solvent was removed and the residue chromatographed over silica gel using ether-ethyl acetate (4:1) as the eluant. The fractions containing the product were combined and concentrated to leave 1.1 g of the above urea as an off-white solid, m.p. 173°-175° C. (dec.)

Workup

  1. customat 25° C.
  2. custom1 hr
  3. customat 55° C., the solvents were removed in vacuo
  4. washwashed with water
  5. customThe solvent was removed
  6. customthe residue chromatographed over silica gel
  7. additionThe fractions containing the product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7f1293c511394cd2a6fef3ae92bebe96
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Reaction notes

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