Phenylethanolamine → 2-Nitromethylene-5-phenyl-oxazolidine

HRID 892787Notes

Reaction equation

HRID 892787 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:10])[CH2:8][NH2:9])=[CH:3][CH:2]=1.CS[C:13](SC)=[CH:14][N+:15]([O-:17])=[O:16]>C(O)C.C1(C)C(C)=CC=CC=1>[N+:15]([CH:14]=[C:13]1[NH:9][CH2:8][CH:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[O:10]1)([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 1000PhenylethanolamineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 678971662-Nitromethylene-5-phenyl-oxazolidineYield 56.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7237O-XyleneSolvent2×

Procedure

In a mixture of 60 ml of ethanol and 200 ml of xylene was dissolved 40 g of DL-β-hydroxyphenethylamine, and the resulting solution was added dropwise to a solution of 57.8 g of 1,1-bis(methylthio)-2-nitroethene in 600 ml of xylene under reflux over a period of 1.5 hours to effect reaction. During the reaction, the low-boiling fractions were gradually removed by distillation and the reaction temperature was maintained at 130° C. to 140° C. After completion of the reaction, crystals were deposited with stirring under ice-cooling. The crystals deposited were collected by filtration, dried, and then mixed with 200 ml of a 5% (by weight) aqueous sodium hydroxide solution. After a slight amount of insolubles were removed by filtration, the filtrate was adjusted to pH 6 with a 10% (by weight) aqueous acetic acid solution, and the crystals deposited were collected by filtration and dried to obtain 34 g of 2-nitromethylene-5-phenyloxazolidine having a melting point of 139°-141° C.

Workup

  1. temperatureunder reflux over a period of 1.5 hours
  2. customreaction
  3. customDuring the reaction
  4. customthe low-boiling fractions were gradually removed by distillation
  5. temperaturethe reaction temperature was maintained at 130° C. to 140° C
  6. customAfter completion of the reaction, crystals
  7. temperaturecooling
  8. filtrationThe crystals deposited were collected by filtration
  9. customdried
  10. additionmixed with 200 ml of a 5% (by weight) aqueous sodium hydroxide solution
  11. customAfter a slight amount of insolubles were removed by filtration
  12. filtrationthe crystals deposited were collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-842dee5ecbd847a29484779d377bb4f3
Source dataset
uspto-grants-1992_06
Patent number
US05120746

Reaction notes

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