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

HRID 1092311ノート

反応式

HRID 1092311 の反応式
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

参加物

5

反応物 3

HCID 6571ChloroacetoneHCID 69828CyclopropylamineHCID 11378442Potassium cyanate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f714a0da80f74e89926c7330a040aed3
出典データセット
uspto-grants-2012_03
特許番号
US08129423B2

反応ノート

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