Ethylenediamine → HCID 86672882, compound

HRID 1616956Notes

Reaction equation

HRID 1616956 reaction equation
[C:1]([O:6][CH2:7][C:8]([F:11])([F:10])[F:9])(=[O:5])[C:2]([O-:4])=O.[CH2:12]([NH2:15])[CH2:13][NH2:14]>FC(F)(F)CO>[F:9][C:8]([F:11])([F:10])[CH2:7][O:6][C:1](=[O:5])[C:2]([NH:14][CH2:13][CH2:12][NH:15][C:2](=[O:4])[C:1]([OH:6])=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 86337708HCID 86337708, compound

Product 1

HCID 86672882HCID 86672882, compound

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent2×

Procedure

A 500 mL 3-neck round bottom flask equipped with a magnetic stirbar, thermocouple, and argon inlet was charged with 2,2,2-trifluoroethyl oxalate (from Preparatory Example P7) (152.5 grams) and 2,2,2-trifluoroethanol (150 grams). The contents were cooled in an ice bath, and a mixture of ethylene diamine (EDA) (3.606 grans) in 2,2,2-trifluoroethanol (40 grams) was added dropwise over a period of 75 minutes. The cooling bath was removed, and the contents were stirred for 18 hours, after which time methyl tert-butyl ether (100 mL) was added, and the solids were then collected via filtration. The resulting 10.2 grams of solids was recrystallized from boiling 2,2,2-trifluoroethanol (416 grams) to obtain 9.23 grams of ethylene-bis-oxamic acid trifluoroethyl ester as white crystals having a melting point of 223° C. 1H NMR (300 MHz, d6-DMSO) δ 9.18 (brs, 2H), 4.92 (q, J=8.9 Hz, 4H), 3.31-3.29 (m, 4H).

Workup

  1. customA 500 mL 3-neck round bottom flask equipped with a magnetic stirbar
  2. temperatureThe contents were cooled in an ice bath
  3. additionwas added dropwise over a period of 75 minutes
  4. customThe cooling bath was removed
  5. additionafter which time methyl tert-butyl ether (100 mL) was added
  6. filtrationthe solids were then collected via filtration
  7. customThe resulting 10.2 grams of solids was recrystallized

Sources & evidence

ORD record
ord-f515db579bcc4b668b08cdeabc94f51d
Source dataset
uspto-grants-2014_07
Patent number
US08765881B2

Reaction notes

Loading…