Methyl iodide → HCID 22880427, compound

HRID 1740684Notes

Reaction equation

HRID 1740684 reaction equation
[CH3:1]I.[CH2:3]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C@H:25]([OH:53])[CH2:26][O:27][CH2:28][C:29]([O:32][C:33]([F:52])([F:51])[C:34]([F:50])([F:49])[O:35][C:36]([F:48])([F:47])[C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40])([F:31])[F:30])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+]>CN(C)C=O.O>[CH2:3]([C:11]1[CH:16]=[N:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][C@H:25]([O:53][CH3:1])[CH2:26][O:27][CH2:28][C:29]([O:32][C:33]([F:52])([F:51])[C:34]([F:49])([F:50])[O:35][C:36]([F:47])([F:48])[C:37]([F:45])([F:46])[C:38]([F:43])([F:44])[C:39]([F:40])([F:41])[F:42])([F:30])[F:31])=[CH:21][CH:22]=2)=[N:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10941720HCID 10941720, compound

Product 1

HCID 22880427HCID 22880427, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (1.1 g, 7.76 mmol) was added to a solution of 5-octyl-2-[4-((R)-2-hydroxy-3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2,-difluoroethoxy)propoxy)phenyl]pyrimidine (Example 4, 1.5 g, 1.94 mmol) and sodium hydride (116 mg, 60 weight percent in oil, 2.91 mmol) in dimethyl formamide (10 ml). The resulting mixture was stirred at room temperature for 10 hours, was diluted with 50 ml of water, and was extracted with three 50 ml aliquots of diethyl ether. The organic extracts were dried (over MgSO4), filtered, and concentrated. The resulting product was then recrystallized from methanol at -30° C. to give a white smectic material.

Workup

  1. extractionwas extracted with three 50 ml aliquots of diethyl ether
  2. dry with materialThe organic extracts were dried (over MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting product was then recrystallized from methanol at -30° C.
  6. customto give a white smectic material

Sources & evidence

ORD record
ord-d7ee0740f10847368b4ad9d9890ff78d
Source dataset
uspto-grants-1999_10
Patent number
US05972241

Reaction notes

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