Hydrazine → HCID 178486503, compound

HRID 1714431Notes

Reaction equation

HRID 1714431 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 178486503HCID 178486503, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5,6dimethoxyindan-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).

Workup

  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

Sources & evidence

ORD record
ord-ccde5cebcf3e4e30b86000b8f85aaa6b
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Reaction notes

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