Water → HCID 19806391, compound

HRID 1681341Notes

Reaction equation

HRID 1681341 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[NH2:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20].O>CO>[OH:9][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH:8]([NH:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 735613-Amino-1,2-propanediolHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 19806391HCID 19806391, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of trans-stilbene oxide (3.93 g, 0.20 mol) and 1-amino-2,3-propanediol (5.46 g, 0.060 mol) was heated at 125° C. for 18 hours in an oil bath. After cooling, the reaction mixture was dissolved in 20 mL of methanol and the solution poured into 150 mL of water. The product separated from the solution as a viscous cream-colored oil that slowly solidified. The solid was collected by filtration and vacuum dried at 40° C. for 18 hours to give 3.81 g (66% yield) of material. The product was recrystallized from methanol-isopropyl ether to give 1.75 g; mp 161°-163° C.

Workup

  1. temperatureAfter cooling
  2. customThe product separated from the solution as a viscous cream-colored oil that
  3. filtrationThe solid was collected by filtration and vacuum
  4. customdried at 40° C. for 18 hours

Sources & evidence

ORD record
ord-9050d6cde0904f2db5ad04a5526daf42
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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