Cetyl Alcohol → HCID 13061617, compound

HRID 1679349Notes

Reaction equation

HRID 1679349 reaction equation
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Na].Cl[C:20]1[N:25]=[C:24](Cl)[C:23]([F:27])=[CH:22][N:21]=1>CCOCC>[CH2:1]([O:17][C:20]1[N:25]=[C:24]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:23]([F:27])=[CH:22][N:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 2682Cetyl AlcoholHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 5360545Sodium2×

Product 1

HCID 13061617HCID 13061617, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 36.3 g quantity of n-hexadecanol is dissolved in 200 ml of absolute ether, 3.3 g of metal sodium is added to the solution and the mixture is refluxed until the sodium has been completely dissolved. Subsequently 8.5 g of 2,4-dichloro-5-fluoropyrimidine is added to the solution, and the mixture is refluxed for 3 hours. The resulting reaction mixture is washed with a small amount of water, and the ethereal layer is concentrated to separate out crystals, which are recrystallized from ethanol to give 18.6 g of white crystalline 2,4-di(n-hexadecyloxy)-5-fluoropyrimidine in a yield of 63.1 %, m.p. 62°-63° C.

Workup

  1. dissolutionhas been completely dissolved
  2. temperaturethe mixture is refluxed for 3 hours
  3. customThe resulting reaction mixture
  4. washis washed with a small amount of water
  5. concentrationthe ethereal layer is concentrated
  6. customto separate out crystals, which
  7. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-2250369e127b4659ad131a42eef446ee
Source dataset
uspto-grants-1978_03
Patent number
US04080455

Reaction notes

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