Hydrochloric Acid → 6-Chloro-1-methyl-3-n-octyl-uracil

HRID 1650125Notes

Reaction equation

HRID 1650125 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:10][C:11]1[N:16]([CH3:17])[C:15](=[O:18])[NH:14][C:13](=[O:19])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C)C=O>[Cl:10][C:11]1[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:13](=[O:19])[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 3015589Uracil, 6-chloro-1-methyl-

Product 1

HCID 230536246-Chloro-1-methyl-3-n-octyl-uracil

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Next 5.4 ml of n-octyl bromide was added to a solution consisting of 5 grams of 6-chloro-1-methyl-uracil obtained as described above, 5.2 grams of potassium carbonate and 50 ml of N,N-dimethylformamide and the mixture was heated to 90° C. and stirred for a period of 5 hours. After cooling, the reaction mixture was added slowly to a solution of 10 ml of concentrated hydrochloric acid and 300 ml of water. The resulting solution was extracted twice with 100 ml of chloroform and, after drying over magnesium sulfate, the chloroform layer was concentrated under reduced pressure. The concentrate was then refined using silica gel column chromatography, whereupon 3.1 grams of 6-chloro-1-methyl-3-n-octyl-uracil was obtained in the form of white crystals.

Workup

  1. customobtained
  2. temperatureAfter cooling
  3. extractionThe resulting solution was extracted twice with 100 ml of chloroform
  4. dry with materialafter drying over magnesium sulfate
  5. concentrationthe chloroform layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d2e62a0e53d043f4972f5250144a878a
Source dataset
uspto-grants-1990_05
Patent number
US04923789

Reaction notes

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