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

HRID 2194818

반응식

HRID 2194818 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-681b4d5f567f41959067b30a94a6281e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334313B2

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