2-[(2-Butoxyphenoxy)methyl]oxirane → HCID 23349132, compound

HRID 1855811Notes

Reaction equation

HRID 1855811 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:2]1[O:4][CH2:3]1.C([NH:24][CH2:25][CH2:26][NH:27][C:28]1[N:33]([CH3:34])[C:32](=[O:35])[N:31]([CH3:36])[C:30](=[O:37])[CH:29]=1)C1C=CC=CC=1>C(O)C>[CH2:13]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:1][CH:2]([OH:4])[CH2:3][NH:24][CH2:25][CH2:26][NH:27][C:28]1[N:33]([CH3:34])[C:32](=[O:35])[N:31]([CH3:36])[C:30](=[O:37])[CH:29]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 202492762-[(2-Butoxyphenoxy)methyl]oxiraneHCID 23349122HCID 23349122, compound

Product 1

HCID 23349132HCID 23349132, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.5 g of 2-n-butoxyphenyl glycidyl ether ##STR27## are heated under reflux together with 5.8 g of N-benzyl-N'-[1,3-dimethyl-2,4-dioxopyrimid-6-yl]ethylenediamine ##STR28## (in 150 ml of ethanol) for 2 hours. The resulting solution is then cooled and concentrated in vacuo. A resinous residue remains. This residue is dissolved in 150 ml of dioxane (without further purification) and then hydrogenated with H2 in the presence of Pd/C at 20° C. for 10 hours. The catalyst is then filtered of; the filtrate is concentrated; and the residue is recrystallized once from toluene. N-[3-(o-Butoxyphenoxy)-2-hydroxypropyl]-N'-[1,3-dimethyl-2,4-dioxopyrimid-6-yl]ethylenediamine of the formula ##STR29## is thus obtained.

Workup

  1. temperatureThe resulting solution is then cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThis residue is dissolved in 150 ml of dioxane (without further purification)
  4. filtrationThe catalyst is then filtered of
  5. concentrationthe filtrate is concentrated
  6. customand the residue is recrystallized once from toluene

Sources & evidence

ORD record
ord-e191f19071ee4374b0d1224343a18eff
Source dataset
uspto-grants-1980_08
Patent number
US04216314

Reaction notes

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