Ethanolamine → 2-(Nitromethylidene)-1,3-oxazolidine

HRID 1259382Notes

Reaction equation

HRID 1259382 reaction equation
CS[C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[CH2:10]([CH2:12][NH2:13])[OH:11].C(OC(=O)C)C>C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:5]([CH:4]=[C:3]1[NH:13][CH2:12][CH2:10][O:11]1)([O-:7])=[O:6]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 8857Ethyl AcetateHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 671951142-(Nitromethylidene)-1,3-oxazolidineYield 259.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

p-Toluene sulfonic acid (0.5 g) was added to a boiling solution of 1,1-bis-methylsulfanyl-2-nitro-ethene (I-1b: 20 g, 12.13 mol) in ethanol (200 mL). This was followed by the addition of ethanolamine (7.4 g, 12.13 mmol) and the resulting mixture was heated to reflux for 12 hours. The reaction mixture was monitored by TLC (100% ethylacetate). The reaction mixture was concentrated, 300 mL of water added and resultant filtered. The filtrate was further concentrated and was followed by the addition of acetone. The reaction mixture was refluxed for 1 hour, cooled to room temperature, and filtered. The acetone layer was concentrated to afford 4.1 g of the crude product which was used in the next step without further purification.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated
  4. addition300 mL of water added
  5. filtrationresultant filtered
  6. concentrationThe filtrate was further concentrated
  7. additionwas followed by the addition of acetone
  8. temperatureThe reaction mixture was refluxed for 1 hour
  9. filtrationfiltered
  10. concentrationThe acetone layer was concentrated

Sources & evidence

ORD record
ord-4f5ff2845dc04f47a22dcf85e5b7f1b8
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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