Chloroacetone → Cyclopropyl-5-methyl-1,3-dihydro-imidazol-2-one

HRID 1092311노트

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HRID 1092311 반응식
Cl[CH2:2][C:3](=O)[CH3:4].[O-:6][C:7]#[N:8].[K+].[CH:10]1([NH2:13])[CH2:12][CH2:11]1>CN(C=O)C>[CH:3]1([N:8]2[C:11]([CH3:12])=[CH:10][NH:13][C:7]2=[O:6])[CH2:4][CH2:2]1

참가 물질

5

반응물 3

HCID 6571ChloroacetoneHCID 69828CyclopropylamineHCID 11378442Potassium cyanate

생성물 1

HCID 55300021Cyclopropyl-5-methyl-1,3-dihydro-imidazol-2-one수율 35.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

Chloroacetone (2.0 g), potassium cyanate (1.84 g) and cyclopropylamine (6.17 g) were dissolved or suspended in DMF (25 mL) and heated to 50° C. over night. The appearance of the suspension changed and on the second day a fine precipitate was observed. The suspension was concentrated in vacuo and the residue was treated with 25% HCl (25 mL) and DCM (50 mL) for one hour with vigorous stirring. The layers were separated and the organic phase was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography using a gradient of methanol in ethyl acetate (0 to 5%) as an eluent to give 1-cyclopropyl-5-methyl-1,3-dihydro-imidazol-2-one as colorless solid (1.05 g). 1H-NMR (δ, CDCl3): 9.80 (br s, 1H), 5.79 (d, J=1.2 Hz, 1H), 2.91 (m, 1H), 2.012 (d, J=1.2 Hz, 3H), 0.92-0.84 (m, 2H), 0.82-0.77 (m, 2H).

후처리

  1. concentrationThe suspension was concentrated in vacuo
  2. additionthe residue was treated with 25% HCl (25 mL) and DCM (50 mL) for one hour with vigorous stirring
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-f714a0da80f74e89926c7330a040aed3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129423B2

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