Water → HCID 57141471, compound

HRID 1977821Notes

Reaction equation

HRID 1977821 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[N:19][N:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]2.CI.O>O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C.O1CCCC1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[N:19][N:20]([CH3:22])[CH3:21])[CH:14]([CH3:1])[CH2:13]2

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 57200018N'-(5-chloroindan-1-ylidene)-N,N-dimethylhydrazine

Product 1

HCID 57141471HCID 57141471, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-40 °C

Procedure

33.1 ml of a 2M solution of lithium diisopropylamide in THF/heptane/ethylbenzene are added dropwise to 300 ml of dry tetrahydrofuran (THF) under argon. At −70° C., 12 g of N′-(5-chloroindan-1-ylidene)-N,N-dimethylhydrazine, dissolved in 100 ml of dry THF, are added dropwise to this solution. After the reaction mixture has been stirred at −70° C. for 1 h and at −40° C. for a further 3 h, 3.882 ml of methyl iodide are added dropwise and the mixture is stirred further overnight. 200 ml of water are added dropwise to the reaction mixture which has warmed to room temperature; the THF is removed in vacuo, and the residue is extracted with ethyl acetate. The ethyl acetate extract is treated with active carbon, dried over sodium sulfate, filtered, concentrated in vacuo and chromatographed on silica gel with ethyl acetate/heptane ½. N′-(5-chloro-2-methylindan-1-ylidene)-N,N-dimethylhydrazine is obtained as an oil.

Workup

  1. additionare added dropwise to this solution
  2. stirringthe mixture is stirred further overnight
  3. temperaturehas warmed to room temperature
  4. customthe THF is removed in vacuo
  5. extractionthe residue is extracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. additionis treated with active carbon
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customchromatographed on silica gel with ethyl acetate/heptane ½

Sources & evidence

ORD record
ord-e6fdbc80403b4d11b87521a811fc317a
Source dataset
uspto-grants-2001_05
Patent number
US06235763B1

Reaction notes

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