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

HRID 1857769
ノート
印刷プレビュー

反応式

HRID 1857769 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 22130832HCID 22130832、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒
2 回

反応条件

温度
-40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-29c51dbf78ef4a2f88f60fbbc6588a3e
出典データセット
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06147097

反応ノート

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