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Potassium Carbonate → 1-(4-Methyl-5-(oxazol-5-yl)thiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)-imidazolidin-2-one

HRID 560860
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HRID 560860 반응식
[CH3:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:10]2=[O:25])[S:5][C:6]=1[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].S([CH2:42][N+:43]#[C-:44])(C1C=CC(C)=CC=1)(=O)=O>CO.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:10]2=[O:25])[S:5][C:6]=1[C:7]1[O:8][CH:44]=[N:43][CH:42]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 580314234-Methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carbaldehyde

생성물 1

HCID 580316541-(4-Methyl-5-(oxazol-5-yl)thiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)-imidazolidin-2-one수율 47%

시약·촉매·용매 2

HCID 887Methanol
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carbaldehyde (0.32 g, 0.86 mmol) in methanol (20 mL) was added potassium carbonate (0.30 g, 2.17 mmol) and tosylmethyl isocyanide (0.23 g, 1.17 mmol). The reaction mixture was stirred at ambient temperature for 1 h, heated to reflux for 1 h, and then cooled to ambient temperature. The mixture was diluted with ethyl acetate, washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a colorless solid in 47% yield (0.32 g): mp 160-162° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.85 (s, 1H), 7.59 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.07 (s, 1H), 4.53 (s, 2H), 4.12-4.06 (m, 2H), 3.49-3.44 (m, 2H), 2.43 (s, 3H); 1H NMR (75 MHz, CDCl3) δ 157.5, 155.6, 149.8, 145.4, 145.1, 139.8, 130.5, 128.5, 125.9, 122.4, 122.1, 111.7, 47.6, 42.1, 42.0, 16.7; MS (ES+) m/z 409.1 (M+1).

후처리

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. temperaturecooled to ambient temperature
  4. washwashed with water and brine
  5. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-76836e364e694849a84c6b22f0eb3024
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063084B2

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