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Water → (4-Diethoxyphosphoryloxyimino-cyclohexa-2,5-dienylidene)-2,4-dichlorophenyl-acetonitrile

HRID 1018893
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HRID 1018893 반응식
[OH:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:10]#[N:11])[CH:5]=[CH:4]1.C(N([CH2:25][CH3:26])CC)C.C([P:29](Cl)(CC)=[O:30])C.[OH2:34].C1C[O:38][CH2:37][CH2:36]1>C(OCC)(=O)C>[CH2:37]([O:38][P:29]([O:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:10]#[N:11])[CH:5]=[CH:4]1)([O:30][CH2:25][CH3:26])=[O:34])[CH3:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5195381Diethylphosphinoyl chlorideHCID 18398532(4-Hydroxyimino-cyclohexa-2,5-dienylidene)-2,4-dichlorphenyl-acetonitrile

생성물 1

HCID 18398561(4-Diethoxyphosphoryloxyimino-cyclohexa-2,5-dienylidene)-2,4-dichlorophenyl-acetonitrile

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

20.4 g (0.07 mol) of (4-hydroxyimino-cyclohexa-2,5-dienylidene)-2,4-dichlorphenyl-acetonitrile, 7.1 g (0.07 mol) of triethylamine and a catalytic amount of N,N-dimethylaminopyridine are dissolved in 270 ml of THF. This solution is cooled in an ice bath, and 12.1 g (0.07 mol) of diethylphosphoryl chloride are added dropwise while stirring. When the addition is complete, the orange solution is warmed to room temperature and stirred overnight. Water and ethyl acetate are subsequently added, and the organic layer is washed several times with saturated sodium chloride solution and water and dried over magnesium sulfate. Evaporation of the solvent gives 30.4 g of a viscous yellowish oil, which is further purified by filtration over silica gel (eluent: hexane/ethyl acetate 9:1). Yield: 25.5 g (85%). 31P-NMR (CDCl3; δ relative to H3PO4 as external reference): 0.132 and 0.003 ppm (P(V) of the (E) and (Z)-isomers). 1H-NMR (CDCl3, δ [ppm]): 7.60-7.15 (m, 7H); 7.0-6.55 (m, 2H), 4.35-4.15, (m, 4H-C(1′)); 1.38 and 1.35 (t, 3H-C(2′)).

후처리

  1. temperatureThis solution is cooled in an ice bath
  2. additionWhen the addition
  3. stirringstirred overnight
  4. washthe organic layer is washed several times with saturated sodium chloride solution and water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-e24bb00e0949495faef2497c675f9a16
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06485886B1

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