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

HRID 904170

반응식

HRID 904170 반응식
[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

참가 물질

6

반응물 3

HCID 588creatinineHCID 962WaterHCID 233337675-Methoxy-2-thienyl isocyanate

생성물 1

HCID 1361999401-(5-Methoxy-2-thienyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea수율 3.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

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.).

후처리

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

출처 및 근거

ORD 기록
ord-727cc847b9654cd5a34f73a1a58857fc
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04230713

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