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Tetrahydrofuran → 1H-Imidazole-1,2-diethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, dicarbamate (ester)

HRID 1857769
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HRID 1857769 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][OH:17])[C:13]([CH2:18][CH2:19][OH:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)C([N:28]=[C:29]=[O:30])=O.C([N:35]([CH2:38]C)CC)C.[O:40]1CCCC1>O>[C:38]([O:17][CH2:16][CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([CH:21]([CH3:23])[CH3:22])[N:12]=[C:13]1[CH2:18][CH2:19][O:20][C:29](=[O:30])[NH2:28])(=[O:40])[NH2:35]
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참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 22130832HCID 22130832, 화합물

생성물 1

HCID 4740821H-Imidazole-1,2-diethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, dicarbamate (ester)수율 81%

시약·촉매·용매 1

HCID 962
Water
용매
2회

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온도
-40 °C

실험 절차

In 10 ml of dry tetrahydrofuran was dissolved 1.01 g (2.7 mmol) of the diol (131c). The solution was cooled to -40° C. and 1.52 g (8 mmol) of trichloroacetyl isocyanate was added dropwise. After 5 minutes, the temperature was allowed to increase gradually to room temperature and the mixture was stirred for 1 hour. Then, 2 ml of triethylamine and 4 ml of water were added and the mixture was heated at 50° C. for 3 hours. The reaction mixture was diluted with water and 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 (5% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 1.0 g (yield 81%) of Compound I-147 as crystals. mp 152-1530° C.

후처리

  1. temperatureto increase gradually to room temperature
  2. temperaturethe mixture was heated at 50° C. for 3 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 (5% methanol-ethyl acetate)
  9. customrecrystallized from ethyl acetate-n-hexane

출처 및 근거

ORD 기록
ord-29c51dbf78ef4a2f88f60fbbc6588a3e
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06147097

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