Styrene Oxide → HCID 54385785, compound

HRID 1462366Notes

Reaction equation

HRID 1462366 reaction equation
[C:1]1([CH:7]2[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH:11]([CH3:24])[CH2:12][O:13][C:14]1[CH:15]=[C:16]([OH:23])[C:17](=[CH:21][CH:22]=1)[C:18]([NH2:20])=[O:19]>CC(O)C>[C:18]([C:17]1[CH:21]=[CH:22][C:14]([O:13][CH2:12][CH:11]([NH:10][CH2:8][CH:7]([OH:9])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:24])=[CH:15][C:16]=1[OH:23])(=[O:19])[NH2:20]

Participants

4

Reactant 2

HCID 7276Styrene OxideHCID 20452664HCID 20452664, compound

Product 1

HCID 54385785HCID 54385785, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 0,96 g of phenyl-ethylene oxide and 2.1 g of 4-(2-amino-propoxy)-salicylamide in 25 ml of 2-propanol is refluxed for 15 hours. The reaction mixture is then evaporated, the residue is partitioned between 10 ml of water and 100 ml of ethyl acetate and the organic phase is washed three times with water. On drying over magnesium sulfate and evaporating the organic phase, crude α-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethyl]-aminomethyl]-benzyl alcohol is obtained and this is recrystallised analogously to Example 2 and in this way gives the two enantiomer pairs with a melting point of 171°-173° and 149°-151° respectively.

Workup

  1. temperatureis refluxed for 15 hours
  2. customThe reaction mixture is then evaporated
  3. customthe residue is partitioned between 10 ml of water and 100 ml of ethyl acetate
  4. washthe organic phase is washed three times with water
  5. dry with materialOn drying over magnesium sulfate
  6. customevaporating the organic phase

Sources & evidence

ORD record
ord-3243c15d65b04460ada1faeacd5a6aa1
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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