Trityl chloride → methyl 1-trityl-1H-1,2,4-triazole-3-carboxylate

HRID 720633ノート

反応式

HRID 720633 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:9]=[CH:8][NH:7][N:6]=1)=[O:4].[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:6]=1)=[O:4]

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178499122HCID 178499122、化合物

生成物 1

HCID 58739241methyl 1-trityl-1H-1,2,4-triazole-3-carboxylate収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A solution of 1H-[1,2,4]triazole-3-carboxylic acid methyl ester (3.0 g, 0.023 mol) in N,N-dimethylformamide at 25° C. was treated with triphenylmethylchloride (7.2 g, 0.025 mol) and triethylamine (6.41 mL, 0.046 mol). The reaction was stirred at 25° C. for 4 days. At this time, the reaction was concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with a dilute 1N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solids were diluted with ether, collected by filtration, washed with ether, and dried in vacuo to afford 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester (2.45 g, 84%) as a white solid: LR-FAB for C23H19N3O2 (M+H)+ at m/z=370.

後処理

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with a dilute 1N aqueous hydrochloric acid solution
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe resulting solids were diluted with ether
  8. filtrationcollected by filtration
  9. washwashed with ether
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-45554a71c9b04e99a924dde2c7ce2c92
出典データセット
uspto-grants-2006_11
特許番号
US07135475B2

反応ノート

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