Water → (5,6-Dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone oxime

HRID 1018125ノート

反応式

HRID 1018125 の反応式
[O:1]1[CH2:6][CH2:5][O:4][C:3]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=O)=[N:2]1.Cl.[NH2:17][OH:18].O>CN(C)C=O>[O:1]1[CH2:6][CH2:5][O:4][C:3]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:17][OH:18])=[N:2]1

参加物

5

反応物 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 11127466(5,6-Dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone

生成物 1

HCID 136333718(5,6-Dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone oxime収率 60.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

At 80° C., 4.14 g (0.02 mol) of (5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone (III-1) in 20 ml of dimethylformamide are stirred with 2.1 g (0.03 mol) of hydroxylamine hydrochloride for 2 hours. The reaction mixture is poured into water and the resulting mixture is extracted with ethyl acetate, and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. 4.7 g of crude product consisting of 15% E isomer and 57.5% Z isomer (HPLC) are obtained. The crude product is chromatographed over silica gel using a mixture of diethyl ether and petroleum ether (1:1). 2.7 g (60.8% of theory) of (5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone oxime (V-1) are obtained (content according to HPLC analysis: 93.4%).

後処理

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customare obtained
  5. customThe crude product is chromatographed over silica gel using
  6. additiona mixture of diethyl ether and petroleum ether (1:1)

出典と根拠

ORDレコード
ord-8990c9501402414ab767f9534c3e552f
出典データセット
uspto-grants-2002_11
特許番号
US06479675B1

反応ノート

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