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Water → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, carbamate (ester)

HRID 1857759
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HRID 1857759 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][CH2:23][OH:24])=[N:12][C:11]=2[CH:25]([CH3:27])[CH3:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:30]([N:32]=C=O)=[O:31].O.C(N(CC)CC)C>O1CCCC1>[C:30]([O:24][CH2:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:25]([CH3:27])[CH3:26])[N:12]=1)(=[O:31])[NH2:32]
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HCID 962WaterHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 4740651H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-

생성물 1

HCID 4740661H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, carbamate (ester)수율 83.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

In 10 ml of dry tetrahydrofuran was dissolved 1.0 g (2.4 mmol) of the alcohol compound (123b), and the mixture was cooled to -20° C., followed by addition of 540 mg (2.9 mmol) of trichloroacetylisocyanate. After 3 minutes, the mixture was warmed to 0° C. and stirred for 10 minutes. There were added 4 ml of water and 2 ml of triethylamine, and the mixture was warmed at 50° C. for 2 hours. The mixture was diluted with ice-water, extracted with ethyl acetate, the extract was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% methanol/ethyl acetate), and recrystallized from ethyl acetate to give 930 mg of Compound I-138 as crystals (yield 85%). mp 189-191° C.

후처리

  1. temperaturethe mixture was warmed to 0° C.
  2. temperaturethe mixture was warmed at 50° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (10% methanol/ethyl acetate)
  9. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-a7115eca5d1c46ca9f1fa9ad73533c25
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06147097

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