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p-Toluenesulfonic acid monohydrate → HCID 178456639、化合物

HRID 2112524
ノート
印刷プレビュー

反応式

HRID 2112524 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=O.[NH2:19][C:20]1[C:21]([CH3:29])=[N:22][N:23]([CH2:26][CH:27]=[CH2:28])[C:24]=1Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[C:3]2[CH:4]=[C:5]([CH3:9])[C:6]([CH3:8])=[CH:7][C:2]=2[N:1]=[C:24]2[N:23]([CH2:26][CH:27]=[CH2:28])[NH:22][C:21]([CH3:29])=[C:20]2[N:19]=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

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57642323(2-Amino-4,5-dimethylphenyl)-(2-chlorophenyl)-methanoneHCID 576423441-Allyl-5-chloro-3-methyl-1H-pyrazol-4-amine

生成物 1

HCID 178456639HCID 178456639、化合物

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
170 °C

実験手順

A mixture of 3.0 g (0.0116 mole) of (2-amino-4,5-dimethylphenyl)-(2-chlorophenyl)-methanone (Xw), 2.0 g (0.0116 mole) of 4-amino-5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole (XIII), 2.21 g (0.0116 mole) of p-toluenesulfonic acid monohydrate and 40 mL of isopropanol was heated in a sealed tube at 170° C. for 90 minutes. The mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and then washed twice with saturated sodium bicarbonate solution. The aqueous washes were reextracted with ethyl acetate, and the combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Trituration of the residue with hexane gave the intermediate 5-(2-chlorophenyl)-1,2-dihydro-3,7,8-trimethyl-1-(2-propenyl)-pyrazolo[3,4-b][1,4]benzodiazepine (XIVw), as a yellow solid. Purification of the filtrates by silica gel chromatography, eluting with ethyl acetate-dichloromethane (1:1) provided additional XIVw and was combined with the material obtained above for a total yield of 2.7 g of XIVw as a yellow solid, which was used directly in the next step.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed twice with saturated sodium bicarbonate solution
  4. dry with materialthe combined ethyl acetate layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3bbc71f711f74dc78a2b57c00e14add3
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07524840B2

反応ノート

読み込み中…

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