18197-26-7

Slightly beige powder

General procedure for the synthesis of sodium dicarbonylammonium from the compound (CAS: 77287-34-4): formamide (0.35 L, 7.8 mol) was slowly added to a stirred mixture of sodium methanol (0.2 kg, 3.7 mol) and N,N-dimethylformamide (DMF, 1.0 L) at below 50 °C. The reaction mixture was heated to 100 °C and the by-product methanol was collected as a distillate. Subsequently, about 0.3 L of solvent was distilled from the reaction mixture under reduced pressure. After cooling the reaction mixture to 30 °C, the precipitated solid was filtered and washed with DMF (0.2 L). Finally, the solid was dried under vacuum at 75 °C to afford sodium dicarbonylammonium (0.3 kg, 85% yield).

Grind the amide under dry tetrahydrofuran (fumehood), filter and wash it with this solvent, then dry it in vacuo. It is soluble in EtOH and H2O but insoluble in Et2O and pet ether. [IR and preparation: Rakshit J Chem Soc 103 1557 1913, Yinglin & Hongwen Synthesis 122 1990, Allenstein & Beyl Chem Ber 100 355 1967, Allenstein et al. Chem Ber 102 4089 1969, Beilstein 2 II 22.]

[1] Synthesis, 1990, # 2, p. 122 - 124
[2] Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8723 - 8730
[3] Journal of Organic Chemistry, 2001, vol. 66, # 9, p. 3238 - 3241
[4] Synthetic Communications, 2015, vol. 45, # 16, p. 1864 - 1870