Ammonia → ammonium N-nitrourethane

HRID 861755Notes

Reaction equation

HRID 861755 reaction equation
[NH3:1].[N+:2]([NH:5][C:6](=[O:10])[O:7][CH2:8][CH3:9])([O-:4])=[O:3].C(Cl)Cl>CO>[N+:2]([NH:5][C:6](=[O:10])[O:7][CH2:8][CH3:9])([O-:4])=[O:3].[NH4+:1]

Participants

5

Reactant 3

HCID 222Ammonia3×HCID 6344DichloromethaneHCID 43970Ethyl N-nitrocarbamate

Product 1

HCID 19704535ammonium N-nitrourethaneYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous NH3 (g) was bubbled into a stirred solution of ethyl N-nitrocarbamate (503.0 g, 3.75 mol, mp 63°-66° C.), CH2Cl2 (1625 mL) and dry CH3OH (825 mL), precooled to 9° C. under N2, until the exothermic reaction subsided (the NH3 addition rate was controlled so as not to exceed a reaction temperature of 23° C.). After the NH3 addition was complete, the mixture was filtered and the collected solid was dried under high vacuum (overnight) to give ammonium ethyl N-nitrocarbamate as colorless crystals (563.0 g, 99%). mp 175°-176° C. IR (KBr) 3230 (s), 3000 (m), 1725 (s) and 1685 (s), 1445 and 1395 (s), 1310 (m), 1220 (s), 1100 (S), 1030 (m) cm-1. 1H NMR (90 MHz, d6 -DMSO) δ 7.30 (bs, 4H, exch D2O), 3.90 (q, 2H, J=4.5 Hz), 1.10 (t, 3H, J=4.5 Hz).

Workup

  1. customprecooled to 9° C. under N2, until the exothermic reaction
  2. customa reaction temperature of 23° C.
  3. filtrationthe mixture was filtered
  4. customthe collected solid was dried under high vacuum (overnight)

Sources & evidence

ORD record
ord-611b9c0e7f724e2c8d9e32327e17f160
Source dataset
uspto-grants-1998_02
Patent number
US05714714

Reaction notes

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