4-Toluenesulfonyl chloride → (S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine

HRID 1534403Notes

Reaction equation

HRID 1534403 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Cl:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][OH:16].[CH2:18]([C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=2)=[N:28][CH:29]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][O:16][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[N:26]=[CH:25][C:24]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:29][N:28]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 641048(S)-3-chlorobutan-1-olHCID 30922104-(5-Hexyl-2-pyrimidinyl)phenol

Product 1

HCID 67801633(S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

26.3 g of (S)-3-chlorobutyl-1-tosylate, preparable from p-toluenesulfonyl chloride and (S)-3-chlorobutan-1-ol, and 27.2 g of 4-(5-n-hexylpyrimidin-2-yl)phenol are added to a suspension of 40 g of potassium carbonate in 200 ml of acetone. After 24 hours' boiling under reflux, the reaction mixture is filtered, the filtrate is free from solvent and the residue is twice recrystallized from ethanol. (S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine is obtained.

Workup

  1. temperatureunder reflux
  2. filtrationthe reaction mixture is filtered
  3. customthe residue is twice recrystallized from ethanol

Sources & evidence

ORD record
ord-3804a4a5ec1244b3bf4aa92fff2ddf9e
Source dataset
uspto-grants-1992_02
Patent number
US05089168

Reaction notes

Loading…