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4-Isopropoxybenzoic acid → 4-[5-(4-Isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-phenylmethanol

HRID 2242238
ノート
印刷プレビュー

反応式

HRID 2242238 の反応式
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.O[NH:38][C:39](=[NH:48])[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][CH:41]=1>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]2[O:11][N:48]=[C:39]([C:40]3[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][CH:41]=3)[N:38]=2)=[CH:12][CH:13]=1)([CH3:2])[CH3:3]
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 729724-Isopropoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178513316HCID 178513316、化合物

生成物 1

HCID 592043064-[5-(4-Isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-phenylmethanol収率 58.1%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
140 °C

実験手順

A solution of 4-iso-propoxybenzoic acid (2.0 g, 11.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.13 g, 11 mmol), 1-hydroxybenzotriazole hydrate (1.50 g, 11.1 mmol) and DMF (14 mL) was stirred at room temperature for 30 minutes. N-hydroxyl-4-(hydroxylmethyl)benzamidine (1.84 g, 11.1 mmol) was added to the reaction mixture and stirred at 140° C. for 2 hours. The reaction mixture was cooled to room temperature, quenched with water (20 mL) and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with 1N HCl and sat. NaHCO3, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound (2.0 g, 58% yield) as a pale yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water (20 mL)
  3. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  4. washThe combined organic layers were washed with 1N HCl and sat. NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-224ae29159e0485a92ae5945c9663dba
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07671043B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート