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1H-1,2,4-Triazole → HCID 23039725、化合物

HRID 2166413
ノート
印刷プレビュー

反応式

HRID 2166413 の反応式
S([O-])(=O)(=O)C.CS(O[CH2:11][C:12]([O:24][CH2:25][CH3:26])([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[CH2:13][CH2:14][CH3:15])(=O)=O.[Na].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CO>[N:28]1([CH2:11][C:12]([O:24][CH2:25][CH3:26])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH2:13][CH2:14][CH3:15])[CH:32]=[N:31][CH:30]=[N:29]1
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 92571H-1,2,4-Triazole2 回HCID 85257MethanesulfonateHCID 5360545Sodium2 回HCID 23039727HCID 23039727、化合物

生成物 1

HCID 23039725HCID 23039725、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
120 °C

実験手順

The mesylate prepared in accordance with (a) is reacted with the sodium salt of 1,2,4-triazole. This is effected by dissolving 0.83 g of sodium in 30 ml of methanol, adding 2.5 g of 1,2,4-triazole and removing the solvent in vacuo. A solution of 8.55 g of the mesylate in 30 ml of dimethyl sulfoxide is added to the residual sodium salt. After being heated for 5 hours on a bath at 120° C., the mixture is cooled to room temperature and extracted with diethyl ether. The combined extracts are washed with water, dried over sodium sulfate and concentrated in vacuo. Yield of crude product 7.6 g. The crude product is purified by column chromatography (silica gel; 1:4 ethyl acetate/petroleum ether) and affords a colourless oil, which crystallises after a few days. Recrystallisation from 16 ml of petroleum ether gives 3.7 g of the end product. Melting point 67° C. 100 MHz-1H-NMR (CDCl3): δ=7.63 and 7.72 ppm (s, 2H of triazole); 7.0-7.4 ppm (m, 3H, aromatic); 4.8 ppm (m, 2H, --CH2N); 3.2-3.8 ppm (m, 2H, --OCH2 --CH3); 1.7-2.4 ppm (m, 2H, --CH2CH2CH3); 1.3 ppm (t, 3H, --OCH2CH3); 0.7-1.4 ppm (m, 5H, --CH2CH2CH3).

後処理

  1. customremoving the solvent in vacuo
  2. additionA solution of 8.55 g of the mesylate in 30 ml of dimethyl sulfoxide is added to the residual sodium salt
  3. temperaturethe mixture is cooled to room temperature
  4. extractionextracted with diethyl ether
  5. washThe combined extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by column chromatography (silica gel; 1:4 ethyl acetate/petroleum ether)
  9. customaffords a colourless oil, which
  10. customcrystallises after a few days
  11. customRecrystallisation from 16 ml of petroleum ether

出典と根拠

ORDレコード
ord-f1c1c9340a824b388f3bae5f1ca5112f
出典データセット
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04945100

反応ノート

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