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Water → (5-Diethoxythiophosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

HRID 1018890
ノート
印刷プレビュー

反応式

HRID 1018890 の反応式
[OH:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1.[P:18](Cl)([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[S:19].C(N(CC)CC)C.O>C1COCC1>[CH2:21]([O:20][P:18]([O:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1)([O:23][CH2:24][CH3:25])=[S:19])[CH3:22]
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 4

HCID 962WaterHCID 8471TriethylamineHCID 17305O,O-diethyl phosphorochloridothioateHCID 86758612HCID 86758612、化合物

生成物 1

HCID 54211158(5-Diethoxythiophosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

8 g (33 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile, prepared as described in example 7.1, are dissolved in 90 ml of THF and cooled in an ice bath. After adding 6.9 g (36 mmol) of diethyl chlorothiophosphate to the solution, 5.0 g (50 mmol) of triethylamine are added dropwise, keeping the temperature below 50° C. The reaction mixture is stirred at 50° C. for 60 min, then is poured into 100 ml of water, and extracted with ethyl acetate. The organic phase is washed with 0.1N hydrochloric acid solution, water, and sodium chloride solution. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by a recrystallization from 2-PrOH. The product is obtained in the form of a brown solid, melting point 86-87° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.41 (t, 6H), 2.37 (s, 3H), 4.35-4.46 (m, 4H), 6.13 (d, 1H), 6.85 (d, 1H), 7.19-7.38 (m, 4H).

後処理

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 50° C
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with 0.1N hydrochloric acid solution, water, and sodium chloride solution
  6. dry with materialThe organic phase is dried over MgSO4
  7. distillationthe solvent is distilled off
  8. customthe residue is purified by a recrystallization from 2-PrOH
  9. customThe product is obtained in the form of a brown solid, melting point 86-87° C

出典と根拠

ORDレコード
ord-58871eb8ec65494d8f1d1796c104874c
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06485886B1

反応ノート

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