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Citric Acid → HCID 21266052、化合物

HRID 566316
ノート
印刷プレビュー

反応式

HRID 566316 の反応式
[NH:1]([CH:3]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:4])[NH2:2].C(N(CC)CC)C.[CH3:21][O:22][C:23](OC)=[C:24]([C:27]#[N:28])[C:25]#[N:26].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[NH2:28][C:27]1[N:1]([CH:3]([CH2:5][CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:4])[N:2]=[C:23]([O:22][CH3:21])[C:24]=1[C:25]#[N:26]
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

7

反応物 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 110079702-(dimethoxymethylidene)propanedinitrileHCID 12874625HCID 12874625、化合物

生成物 1

HCID 21266052HCID 21266052、化合物収率 80.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 962
Water
溶媒

反応条件

温度
20 °C

実験手順

3.6 g of 2-hydrazino-5-phenylpentane are dissolved in 40 ml of methanol, and 2.8 ml of triethylamine are added. Then, 2.8 g of 1,1-dimethoxy-2,2-dicyanoethylene are added at approx. 0° C. The reaction solution is warmed to approx. 20° C. and stirred for 1.5 hours at approx. 20° C. For work-up, the mixture is diluted with water, acidified with citric acid and extracted twice with dichloromethane. The combined dichloromethane phases are dried with magnesium sulphate and evaporated in vacuo. This gives 5.1 g of a yellow oil, which crystallizes slowly. The oil is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a petroleum ether/ethyl acetate mixture in a ratio of 5:1 to 1:1. This gives a fraction which, after evaporation in vacuo, affords 4.6 g (=80.9% of theory) of 5-amino-4-cyano-3-methoxy-1-[(5-phenyl)-pent-2-yl]-pyrazole.

後処理

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe combined dichloromethane phases are dried with magnesium sulphate
  3. customevaporated in vacuo
  4. customThis gives 5.1 g of a yellow oil, which crystallizes slowly
  5. customThe oil is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a petroleum ether/ethyl acetate mixture in a ratio of 5:1 to 1:1
  6. customThis gives a fraction which
  7. customafter evaporation in vacuo

出典と根拠

ORDレコード
ord-bbcced926d7b49a4a1ad03814ee79b9d
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06174884B1

反応ノート

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