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1-Chloro-4-nitrobenzene → 1-Methyl-4-(4-nitrophenoxy)-3,5-diphenyl-1H-pyrazole

HRID 436611
ノート
印刷プレビュー

反応式

HRID 436611 の反応式
[OH:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4][N:5]([CH3:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1.[OH-].[Na+]>O.CN(C=O)C>[CH3:13][N:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([O:1][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[C:3]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:4]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

7

反応物 4

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 12326421HCID 12326421、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 213980591-Methyl-4-(4-nitrophenoxy)-3,5-diphenyl-1H-pyrazole収率 91.4%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of 4-hydroxy-1-methyl-3,5-diphenylpyrazole (10 g, 0.04 mole), potassium t-butoxide (4.5, 0.04 mole) and dry DMF (150 ml) is stirred and heated to 60° C. The green fluorescent solution is cooled to room temperature and p-chloronitrobenzene (6.0 g, 0.038 mole) is added. The dark green solution is heated at 60° C for 24 hours and then poured into water, made alkaline with 1N sodium hydroxide and extracted with ether. The ether layer is separated, washed well with water, dried and stripped in vacuo to give a bright yellow solid 12.9 g (86.5%), m.p. 85° C to 110° C. The solid is chromatographed on silica gel with benzene to give a yellow crystalline solid 11.3 g, m.p. 74° C to 100° C. Recrystallization from methanol (185 ml) affords white crystals 5.5 g (37%) m.p. 120° C to 122° C.

後処理

  1. temperatureThe green fluorescent solution is cooled to room temperature
  2. temperatureThe dark green solution is heated at 60° C for 24 hours
  3. extractionextracted with ether
  4. customThe ether layer is separated
  5. washwashed well with water
  6. customdried

出典と根拠

ORDレコード
ord-4f62de5c20db4953a164c0d4ada95afe
出典データセット
uspto-grants-1977_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04009277

反応ノート

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