Ethanol → HCID 57738870, compound

HRID 1715734Notes

Reaction equation

HRID 1715734 reaction equation
C(O)C.[Na].[N:5]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:24](OCC)(=[O:30])[C:25](OCC)=[O:26]>C(O)(=O)C.O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][N:5]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:25]([OH:26])[C:24]([OH:30])=[C:6]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 608668HCID 608668, compoundHCID 5360545Sodium2×

Product 1

HCID 57738870HCID 57738870, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a 1000-mL round bottom flask was added containing a stir bar, and argon atmosphere, and outfitted with a reflux condenser was added ethanol (200 proof, 500 mL) and sodium metal (21.31 g, 927 mmol). When the sodium was completely dissolved, a mixture of triethyl nitrilotriacetate (56.20 g, 204 mmol) and diethyl oxalate (29.44 g, 204 mmol) was added. The mixture was refluxed overnight, whereupon it became a clear, gelatinous solution. After cooling to room temperature, the mixture was poured into 1200 mL of DI water, chilled in an ice bath and acidified with glacial acetic acid (200 mL). The resulting white precipitate was isolated via vacuum filtration and washed with several portions of DI water to yield 59.75 g (89%) of a white solid. mp 121.3-121.8° C.; 1H NMR (300 MHz, CDCl3): δ 7.51 (s, 2H), 5.32 (s, 2H), 4.39 (q, 4H, J=7.7 Hz), 4.20 (q, 2H, J=7.7 Hz), 1.38 (t, 6H, J=7.7 Hz), 1.27 (t, 3H, J=7.7 Hz); 13C NMR (75 MHz, CDCl3): δ 169.5, 162.4, 139.6, 111.1, 61.6, 47.9, 14.5, 14.4; HRMS (EI): Calcd for C14H19NO8 ([M]+), 329.1111, found m/z, 329.1111; Anal. Calcd for C14H19NO8: C, 51.06; H, 5.82; N, 4.25%, found: C, 50.79; H, 5.83; N, 4.22%.

Workup

  1. additionTo a 1000-mL round bottom flask was added
  2. additioncontaining a stir bar
  3. customargon atmosphere, and outfitted with a reflux condenser
  4. additionwas added
  5. temperatureThe mixture was refluxed overnight, whereupon it
  6. temperaturechilled in an ice bath
  7. customThe resulting white precipitate was isolated via vacuum filtration
  8. washwashed with several portions of DI water

Sources & evidence

ORD record
ord-16c7c62c802f4c81b5460475c5616712
Source dataset
uspto-grants-2010_09
Patent number
US07799932B2

Reaction notes

Loading…