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4-Bromobenzaldehyde → (S)-N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1525257
ノート
印刷プレビュー

反応式

HRID 1525257 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([S@@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:16]/[S@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[CH:4][CH:3]=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

6

反応物 3

HCID 707414-BromobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-

生成物 1

HCID 42632102(S)-N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide収率 71%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
37 °C

実験手順

To 4-bromobenzaldehyde, 18-a, (50 g, 0.27 mol) in dichloromethane (500 mL) were added (S)-2-methylpropane-2-sulfinamide (43 g, 0.36 mol), PPTS (6.7 g, 0.027 mmol) and anhydrous CuSO4 (131 g, 0.82 mol) and the resulting mixture was stirred at 37° C. overnight. The mixture was then filtrated and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=20/1) to provide the product, 19-a, (70 g, 71%).

後処理

  1. filtrationThe mixture was then filtrated
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=20/1)

出典と根拠

ORDレコード
ord-c24f566e42594576bc866f147ffd6951
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079930B2

反応ノート

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