Diethyl Ether → HCID 86740393, compound

HRID 465053Notes

Reaction equation

HRID 465053 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][NH:6][CH3:7])[CH3:2].[CH2:9](N(CC)CC)C.[Cl:16][C:17](Cl)(CCl)[C:18]#[N:19].C(OCC)C>O1CCCC1>[Cl:16][C:17](=[CH:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:8])[CH3:9])[C:18]#[N:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 131332,2,3-TrichloropropiononitrileHCID 95849Glycine, N-methyl-, ethyl ester

Product 1

HCID 86740393HCID 86740393, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of sarcosine ethyl ester (58.5 g, 0.499 mol), tetrahydrofuran (200 ml) and triethylamine (101.2 g, 1 mol) is added dropwise within 15 minutes to a solution of 2,2,3-trichloropropionitrile (79.0, 0.499 mol) in tetrahydrofuran (200 ml). Within 1 hour, the temperature of the mixture rises spontaneously to 30° C. To complete the reaction, the mixture is then refluxed for 3 hours. It is left to cool, stirred into diethyl ether (4 liters), filtered to remove the precipitated triethylamine hydrochloride and the etheral solution is concentrated. The residue is distilled under high vacuum to give a colorless oil (97.1 g), boiling point 0.3 mm Hg 120°-130° C. containing both isomers in a ratio of approximetely 1:1 according to 1H-NMR spectroscopy. An isomer, presumably the isomer of (E) configuration, crystallises out of this oil occasionally, mp. 57° C.

Workup

  1. customrises spontaneously to 30° C
  2. customthe reaction
  3. temperaturethe mixture is then refluxed for 3 hours
  4. waitIt is left
  5. temperatureto cool
  6. filtrationfiltered
  7. customto remove the precipitated triethylamine hydrochloride
  8. concentrationthe etheral solution is concentrated
  9. distillationThe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-b02f2fea7a794aba9f67be2f82feb21e
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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