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1,2-Dichloroethane → 5-isobutyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazol-2-amine

HRID 881743
ノート
印刷プレビュー

反応式

HRID 881743 の反応式
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.C(N1C=CC=CC1=O)(N1C=CC=CC1=O)=S.[N-:33]=[C:34]=S.[CH3:36][CH:37]([CH3:43])[CH2:38][C:39]([NH:41]N)=[O:40].C(Cl)CCl>C(Cl)Cl>[CH2:38]([C:39]1[O:40][C:34]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[N:33][N:41]=1)[CH:37]([CH3:43])[CH3:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 322833-MethylbutanehydrazideHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 178418790HCID 178418790、化合物

生成物 1

HCID 867008455-isobutyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazol-2-amine
収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (200 mg, 0.91 mmol) in methylene chloride (4.5 ml) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (212 mg, 0.91 mmol) and stirred at room temperature for 1 hour. Upon complete formation of the isothiocyanate, 3-methylbutanehydrazide (159 mg, 1.37 mmol) was added to the mixture and stirred at room temperature for overnight. EDC (315 mg, 1.64 mmol) was then added and the reaction stirred at room temperature for 14 hours. The reaction was concentrated to dryness and taken up in water to form a slurry. The slurry was filtered and washed with water to afford the crude product, which was purified by column chromatography to afford the title compound as off-white solid after drying (217 mg, 69% yield). LC/MS, ESI-MS(+) m/z 344.1, RT 1.45 (Condition R).

後処理

  1. stirringstirred at room temperature for overnight
  2. stirringthe reaction stirred at room temperature for 14 hours
  3. concentrationThe reaction was concentrated to dryness
  4. customto form a slurry
  5. filtrationThe slurry was filtered
  6. washwashed with water
  7. customto afford the crude product, which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-ed005af77e91469691fd62a286bd34c3
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993619B2

反応ノート

読み込み中…

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