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Sodium Hydroxide → 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-thiazol-3-yl]-N-[(E)-methoxyiminomethyl]-2-methylbenzamide

HRID 1522784
ノート
印刷プレビュー

反応式

HRID 1522784 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[S:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:28]OC(OC)N(C)C.Cl.[CH3:37][O:38][NH2:39].[OH-].[Na+]>O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[S:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:20]/[CH:28]=[N:39]/[O:38][CH3:37])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
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 4

HCID 14798Sodium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 521874O-Methylhydroxylamine hydrochlorideHCID 894445764-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide

生成物 1

HCID 1365993504-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-thiazol-3-yl]-N-[(E)-methoxyiminomethyl]-2-methylbenzamide

試薬・触媒・溶媒

2
HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

A solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide (200 mg) and N,N-Dimethylformamide dimethylacetal (4 mL) was refluxed under argon for one hour then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (2 mL) and a solution of O-methylhydroxylamine hydrochloride (2.8 eq.) and sodium hydroxide (6 eq.) in water (1.6 mL) and acetic acid (1.6 mL) was added. The solution was stirred at rt for 10 minutes. It was then quenched by addition of water and extracted with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate and evaporated. Flash Chromatography eluting with Cyclohexane:EtOAc afforded 243 mg of the title compound.

後処理

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 1,4-dioxane (2 mL)
  3. customIt was then quenched by addition of water
  4. extractionextracted with methyl tert-butyl ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. washFlash Chromatography eluting with Cyclohexane

出典と根拠

ORDレコード
ord-f827bf9fbcd54d8e9e3936bc219ec824
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09078444B2

反応ノート

読み込み中…

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