Oxirane, [[4-[2-(2-methylpropoxy)ethoxy]phenoxy]methyl]- → HCID 20222108, compound

HRID 980166Notes

Reaction equation

HRID 980166 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]2[O:16][CH2:15]2)=[CH:10][CH:9]=1.[NH2:20][CH2:21][CH2:22][NH:23][C:24]([N:26]([CH3:28])[CH3:27])=[O:25]>C(O)(C)C>[CH3:27][N:26]([CH3:28])[C:24]([NH:23][CH2:22][CH2:21][NH:20][CH2:15][CH:14]([OH:16])[CH2:13][O:12][C:11]1[CH:17]=[CH:18][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH:2]([CH3:19])[CH3:1])=[CH:9][CH:10]=1)=[O:25]

Participants

4

Reactant 2

HCID 10635469Oxirane, [[4-[2-(2-methylpropoxy)ethoxy]phenoxy]methyl]-HCID 20383014N'-(2-Aminoethyl)-N,N-dimethylurea

Product 1

HCID 20222108HCID 20222108, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8 g of 3-(4-(2-(2-methylpropoxy)ethoxy)phenoxy)-1,2-epoxypropane and 14 g of N-2-aminoethyl-N',N'-dimethylurea was warmed (60°-70° C.) in 150 ml of isopropanol over night. The mixture was evaporated and the residue dissolved in ethyl acetate. The ethyl acetate phase was washed with water (twice), fresh water was then added and pH lowered to 5 with hydrochloric acid. Fresh ethyl acetate was then added to the water phase and pH was rised to 9.5. The organic phase was separated off, dried, and evaporated. The residue was recrystallized from a small amount of ethyl acetate. Yield 3 g. M.p. 75° C. (base). The structure was determined using NMR-analysis.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe ethyl acetate phase was washed with water (twice), fresh water
  4. additionwas then added
  5. additionFresh ethyl acetate was then added to the water phase and pH
  6. customThe organic phase was separated off
  7. customdried
  8. customevaporated
  9. customThe residue was recrystallized from a small amount of ethyl acetate

Sources & evidence

ORD record
ord-54c1b940729641c49eefa387cfa091b9
Source dataset
uspto-grants-1987_01
Patent number
US04636501

Reaction notes

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