Methyl 3-isocyanatobenzoate → methyl-3-[3-(4-isopropylphenyl)-2,5-DIOXO-imidazolidin-1-yl]-benzoate

HRID 600920ノート

反応式

HRID 600920 の反応式
CO[C:3](=[O:15])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[N:16]([C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O:24][CH3:25])=[O:23])=[C:17]=[O:18]>C1(C)C=CC=CC=1>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][CH:28]=[C:19]([N:16]2[C:3](=[O:15])[CH2:4][N:5]([C:6]3[CH:7]=[CH:8][C:9]([CH:12]([CH3:13])[CH3:14])=[CH:10][CH:11]=3)[C:17]2=[O:18])[CH:20]=1

参加物

4

反応物 2

HCID 2733366Methyl 3-isocyanatobenzoateHCID 22669181Methyl-2-(4-isopropylanilino)acetate

生成物 1

HCID 66603600methyl-3-[3-(4-isopropylphenyl)-2,5-DIOXO-imidazolidin-1-yl]-benzoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of methyl-2-(4-isopropylanilino)acetate (1.10 g, 5.31 mmol) in toluene (30 mL) was treated with methyl 3-isocyanatobenzoate (1.03 g), and the resulting solution was stirred at ambient temperature for 20 h. The reaction mixture was evaporated, and a portion (0.6 g) of the resulting solid material used directly in the next step. The compound was dissolved in methanol, and treated with sodium methoxide (0.84 mL of 0.5 M in methanol). The resulting solution was stirred for 1 h, then evaporated and partitioned between water and ethyl acetate (50 mL each). The organic extract was washed with brine, dried over magnesium sulfate, filtered and evaporated. The residual material was separated by preparative thin-layer chromatography (silica gel, 30:70 ethyl acetate-hexane) to afford pure product, methyl-3-[3-(4-isopropylphenyl)-2,5-DIOXO-imidazolidin-1-yl]-benzoate, as a waxy solid. 1H NMR (CDCl3, 300 MHz): δ 8.16 (1H, t, J=1.8 Hz), 8.07 (1H, dt, J=7.6, 1.5 Hz), 7.67 (1H, ddd, J=8.0, 2.0, 1.1 Hz), 7.56 (1H, t, J=7.9 Hz), 7.51 (2H, d, J=8.8 Hz), 7.27 (2H, d, J=8.8 Hz), 4.47 (2H, s), 3.92 (3H, s), 2.91 (1H, m, J=7.0 Hz), 1.25 (6H, d, J=7.0 Hz). Mass spectrum (ES+): m/z 353 (36), 321 (100).

後処理

  1. customThe reaction mixture was evaporated
  2. dissolutionThe compound was dissolved in methanol
  3. additiontreated with sodium methoxide (0.84 mL of 0.5 M in methanol)
  4. stirringThe resulting solution was stirred for 1 h
  5. customevaporated
  6. custompartitioned between water and ethyl acetate (50 mL each)
  7. extractionThe organic extract
  8. washwas washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residual material was separated by preparative thin-layer chromatography (silica gel, 30:70 ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-7ffe5038b8cc450cbd53b46b3bef5e49
出典データセット
uspto-grants-2011_03
特許番号
US07902241B2

反応ノート

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