Water → HCID 54522751、化合物

HRID 48133

反応式

HRID 48133 の反応式
[OH:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:4]#[N:5].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.O>O1CCCC1>[CH3:16][S:17]([O:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)[C:4]#[N:5])(=[O:19])=[O:18]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867593582-Hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile

生成物 1

HCID 54522751HCID 54522751、化合物収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2-hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile (1.8 g; 9 mmol) is dissolved in 15 ml of anhydrous tetrahydrofuran, and cooled to 0° C. Methanesulfonyl chloride (0.93 ml, 0.012 mol) is added at once, followed by triethylamine (2 ml, 0.015 mol) dropwise over 20 min, keeping the temperature of the mixture below 5° C. The mixture is then stirred at 2° C. for 1 h 15 min, and poured into 200 ml of iced water. The suspension is extracted with ethyl acetate, the organic extract is washed neutral with water, then with brine, and dried over magnesium sulfate. Rotary evaporation of the solvent and recrystallization from 80 ml of ethanol yields 2-methylsulfonyloxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile (1.02 g; 41%) as light yellow hair-like crystals, mp 147-152° C. (dec). 1H-NMR reveals the presence of only one isomer.

後処理

  1. customthe temperature of the mixture below 5° C
  2. extractionThe suspension is extracted with ethyl acetate
  3. extractionthe organic extract
  4. washis washed neutral with water
  5. dry with materialwith brine, and dried over magnesium sulfate
  6. customRotary evaporation of the solvent and recrystallization from 80 ml of ethanol

出典と根拠

ORDレコード
ord-212d808d04a24f93b79c9b42fc64dcf5
出典データセット
uspto-grants-2004_03
特許番号
US06703182B1

関連ノート

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