Hydrochloric Acid → HCID 14365841, compound

HRID 2379662Notes

Reaction equation

HRID 2379662 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[K+].[CH2:26]([O:31][CH:32]([CH3:49])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:27][CH2:28][CH2:29][CH3:30].Cl>O.CN(C)C=O>[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH:32]([O:31][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH3:49])=[CH:21][CH:22]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 233663776-Pentyloxyheptyl p-toluenesulfonateHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 14365841HCID 14365841, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Separately, 3.12 g of 5-n-decyl-2-(4-hydroxyphenyl)pyrimidine and 0.53 g of potassium hydroxide were added to 14 ml of dimethylformamide, and the mixture was stirred for 3 hours at 100° C. To the mixture was added the above-prepared 2.98 g of 6-pentyloxyheptyl-p-toluenesulfonate followed by 5 hours of stirring under heating at 100° C. After the reaction, the reaction mixture was poured into 200 ml of cold water and acidified to about pH 3 with 6N-hydrochloric acid and extracted with benzene, followed by washing with water, drying with anhydrous magnesium sulfate and distilling-off of the solvent, to obtain 4.71 g of crude product. The product was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/2) and recrystallized from hexane to obtain 1.56 g of 5-n-decyl-2-[4-(6-pentyloxyheptyloxy)phenyl]pyrimidine.

Workup

  1. waitfollowed by 5 hours
  2. stirringof stirring
  3. temperatureunder heating at 100° C
  4. customAfter the reaction
  5. extractionextracted with benzene
  6. washby washing with water
  7. dry with materialdrying with anhydrous magnesium sulfate and distilling-off of the solvent
  8. customto obtain 4.71 g of crude product
  9. customThe product was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/2)
  10. customrecrystallized from hexane

Sources & evidence

ORD record
ord-b5d1a23de3bc49f9839933cff38ae4e0
Source dataset
uspto-grants-1994_11
Patent number
US05364559

Reaction notes

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