Hydrazine → HCID 178486503, 화합물

HRID 460338

반응식

HRID 460338 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[CH2:7][CH2:6]2.[F:15][C:16]1[CH:17]=[C:18]([N:22]=[C:23]=S)[CH:19]=[CH:20][CH:21]=1.C[Si](C)(C)[Si](C)(C)C.[Li].[NH2:34][NH2:35]>O.C(O)(=O)C.C1COCC1>[F:15][C:16]1[CH:17]=[C:18]([NH:22][C:23]2[NH:35][N:34]=[C:8]3[C:9]4[C:5]([CH2:6][C:7]=23)=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=4)[CH:19]=[CH:20][CH:21]=1

참가 물질

8

반응물 4

HCID 9321HydrazineHCID 98343-Fluorophenyl isothiocyanateHCID 750185,6-Dimethoxy-1-indanoneHCID 57425481Lithium hexamethyldisilane

생성물 1

HCID 178486503HCID 178486503, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 5,6 dimethoxyindan-1-one, Compound 3a, (3.0 g, 0.0154 mole), 3-fluoro-phenyl isothiocyanate, Compound 4a, (2.4 g, 0.0157 mole) and THF (3.0 mL) was added to lithium hexamethyldisilane (15.4 mL, 0.0154 mole) dropwise at room temperature with stirring. The reaction mixture was stirred for 12 hrs. Hydrazine (0.75 mL, 0.0154 mole) and acetic acid (0.96 mL) were added to the reaction mixture, which was then heated at the reflux temperature for 24 hrs. The resulting mixture was first added to water (30 mL) and then extracted with CH2Cl2. The organic layers were combined and washed with aqueous NaHCO3 solution, then washed with water and brine solution, dried (Na2SO4), and solvent was removed in vacuo. The residue was dissolved in hot CH3CN. To the mixture was then added one equivalent of an HCl-ether solution to yield a precipitate of the title compound. The precipitate was dissolved in CH3CN and decolorized with charcoal and re-crystallized to give Compound 14 as an off white solid. MS m/z 326 (M+H)+; 1HNMR (DMSO-d6): 3.44(s, 2H), 3.80(s, 3H), 3.81(s, 3H),6.58(t, 1H),6.85 (d, 1H), 7.1(d, 1H), 7.21(s, 1H), 7.23(s, 1H), 7.3(m, 1H), 9.2(br s, 1H).

후처리

  1. stirringThe reaction mixture was stirred for 12 hrs
  2. temperaturewas then heated at the reflux temperature for 24 hrs
  3. extractionextracted with CH2Cl2
  4. washwashed with aqueous NaHCO3 solution
  5. washwashed with water and brine solution
  6. dry with materialdried (Na2SO4), and solvent
  7. customwas removed in vacuo
  8. dissolutionThe residue was dissolved in hot CH3CN

출처 및 근거

ORD 기록
ord-7b1b746452624cf3b25f7366049bbc14
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196110B2

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