Methyl iodide → HCID 178439121, compound

HRID 904606Notes

Reaction equation

HRID 904606 reaction equation
[C:1]([C:3]1[N:4]=[N:5][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[CH:2].[CH2:20]([Li])CCC.CI.[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[C:1]([C:3]1[N:4]=[N:5][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[C:2][CH3:20]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178436319HCID 178436319, compound

Product 1

HCID 178439121HCID 178439121, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

2.56 g of 3-ethynyl-6-(trans-4-pentylcyclohexyl)pyridazine were dissolved in 25 ml of tetrahydrofuran under nitrogen. The solution was cooled to -70° C. and then 7.5 ml of a 1.6 M solution of butyl lithium in hexane were added dropwise within 20 minutes. The mixture was stirred at -70° C. for a further 1 hour and then 0.74 ml of methyl iodide was added dropwise within 5 minutes. The mixture was stirred overnight and warmed slowly to room temperature. After 15.5 hours, the dark mixture was poured into 100 ml of water and made neutral with solid ammonium chloride. The solution obtained was extracted three times with 100 ml of ether each time. The ether phases were washed twice with 100 ml of water each time, subsequently combined, dried with sodium sulphate, filtered and concentrated on a rotary evaporator. Recrystallization of the resulting dark crystals in ethyl acetate/hexane (1:9) gave 1.87 g (70%) of 3-(1 -propynyl)-6-(trans-4-pentylcyclohexyl)pyridazine as brown crystals of melting point 103°-104° C. and clearing point (S-I) 99.3° C.

Workup

  1. stirringThe mixture was stirred overnight
  2. temperaturewarmed slowly to room temperature
  3. waitAfter 15.5 hours
  4. customThe solution obtained
  5. extractionwas extracted three times with 100 ml of ether each time
  6. washThe ether phases were washed twice with 100 ml of water each time
  7. dry with materialdried with sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. customRecrystallization of the resulting dark crystals in ethyl acetate/hexane (1:9)

Sources & evidence

ORD record
ord-5bdb496f5d2f4563b8af9923a6192a81
Source dataset
uspto-grants-1983_12
Patent number
US04419262

Reaction notes

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