Triethylamine → N-tert-Butyl-alpha-(4-bromophenyl)nitrone

HRID 411787

反応式

HRID 411787 の反応式
Cl.[C:2]([NH:6][OH:7])([CH3:5])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.CCN(CC)CC.[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[C:2]([N+:6]([O-:7])=[CH:13][C:12]1[CH:15]=[CH:16][C:9]([Br:8])=[CH:10][CH:11]=1)([CH3:5])([CH3:4])[CH3:3]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 707414-BromobenzaldehydeHCID 2777896N-tert-butylhydroxylamine hydrochloride

生成物 1

HCID 73166239N-tert-Butyl-alpha-(4-bromophenyl)nitrone

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

By anaolgy to the procedure for the synthesis described above, 5.024 g (40.0 mmol) of N-tert-butylhydroxylamine hydrochloride (1) were reacted with 6.476 g (35.0 mmol) of 4-bromobenzaldehyde (2c) in 100 mL of anhydrous toluene, and in the presence of 4.554 g (45 mmol, 6.27 mL) of Et3N and 8.425 g (70.0 mmol) of MgSO4. Purification of the crude yellow oil by column chromatography (silica gel, EtOAc/hexanes=1:6 to 1:3) yielded 8.95 g (quant.) of colorless crystals. Rf: 0.25 (EtOAc/hexanes=1:4, UV254-quenching). 1H NMR (300 MHz, CDCl3, room temp.): δ8.14 (dt, J=8.7,2.4 Hz, 2H, Ar-H), 7.49 (dt, superimposed, J=8.7,2.4 Hz, 2H, Ar-H), 7.48 (s, superimposed, 1H, HC(═N)), 1.56 (s, 9H, C(CH3)3) ppm. 13C NMR (75 MHz, CDCl3, room temp.): δ131.53, 130.06, 129.81, 128.92, 123.73, 71.09, 28.20 ppm.

後処理

  1. customPurification of the crude yellow oil by column chromatography (silica gel, EtOAc/hexanes=1:6 to 1:3)
  2. customyielded 8.95 g (quant.) of colorless crystals

出典と根拠

ORDレコード
ord-7c51483e7aba4154a35611972a66284f
出典データセット
uspto-grants-2003_05
特許番号
US06559255B2

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