Ethylenediamine → HCID 86672882, compound

Participants

Reaction Steps

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).

Provenance & Evidence