Hydrogen Peroxide → 2,4-Bis{N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-chloro-s-triazine

HRID 1276638ノート

反応式

HRID 1276638 の反応式
OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([OH:36])[C:30]([CH3:38])([CH3:37])[CH2:29]3)[N:20]=[C:19]([Cl:39])[N:18]=2)[CH2:6][C:5]1([CH3:41])[CH3:40].S([O-])([O-])=O.[Na+].[Na+].[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>O.C(OCC)(=O)C>[OH:52][C:48]([CH3:51])([CH3:50])[CH2:49][O:36][N:31]1[C:32]([CH3:35])([CH3:34])[CH2:33][CH:28]([CH2:27][CH2:26][CH2:25][CH2:24][NH:23][C:21]2[N:22]=[C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:7]3[CH2:6][C:5]([CH3:41])([CH3:40])[N:4]([O:3][CH2:49][C:48]([CH3:51])([OH:52])[CH3:50])[C:9]([CH3:11])([CH3:10])[CH2:8]3)[N:18]=[C:19]([Cl:39])[N:20]=2)[CH2:29][C:30]1([CH3:38])[CH3:37]

参加物

7

反応物 4

HCID 784Hydrogen Peroxide2 回HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 570971972,4-bis[N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine

生成物 1

HCID 571517592,4-Bis{N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-chloro-s-triazine収率 99.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
42.5 °C

実験手順

A total of 40 g (0.59 mol) of 50% aqueous hydrogen peroxide is added in two portions over five hours to a mixture of 43.2 g (0.076 mol) of 2,4-bis[N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine and 7.0 g (0.035 mol) of ferrous chloride tetrahydrate in 150 g of tert-butyl alcohol and 15 g of water. Another portion of 50% aqueous hydrogen peroxide (3 g, 0.044 mol) is added to the reaction mixture while the temperature is maintained at 40-45° C. for 2.25 hours. The reaction mixture is diluted with 100 g of ethyl acetate. A solution of 100 g of 20% aqueous sodium sulfite is added and the reaction mixture is heated at 60° C. for one hour to decompose residual peroxide. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are concentrated. The crude product is purified by flash chromatography on silica gel with 1:1 (v/v) hexane/ethyl acetate to afford 54.1 g of the title compound.

後処理

  1. temperaturethe reaction mixture is heated at 60° C. for one hour
  2. extractionThe aqueous layer is extracted with ethyl acetate
  3. concentrationthe combined organic layers are concentrated
  4. customThe crude product is purified by flash chromatography on silica gel with 1:1 (v/v) hexane/ethyl acetate

出典と根拠

ORDレコード
ord-58be3852bd6842ce8f69b23e5266a5d9
出典データセット
uspto-grants-2000_12
特許番号
US06166212

反応ノート

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