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

HRID 1018890
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HRID 1018890 반응식
[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]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 17305O,O-diethyl phosphorochloridothioateHCID 86758612HCID 86758612, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-58871eb8ec65494d8f1d1796c104874c
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06485886B1

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