EP 1218362 A1 20020703 - METHOD FOR PRODUCING 3-ALKYL-N-NITRO-4H-1,3,5-OXADIAZINE-4-IMINES
Title (en)
METHOD FOR PRODUCING 3-ALKYL-N-NITRO-4H-1,3,5-OXADIAZINE-4-IMINES
Title (de)
VERFAHREN ZUR HERSTELLUNG VON 3-ALKYL-N-NITRO-4H-1,3,5-OXADIAZIN-4-IMINEN
Title (fr)
PROCEDE DE PREPARATION DE 3-ALKYL-N-NITRO-4H-1,3,5-OXADIAZIN-4-IMINES
Publication
Application
Priority
- DE 19947332 A 19991001
- EP 0009343 W 20000925
Abstract (en)
[origin: DE19947332A1] 3-Alkyl-N-nitro-4H-1,3,5-oxadiazine-4-imines (I) are produced by neutralization of nitric acid with an alkylamine, reaction of the alkylammonium nitrate obtained with cyanamide, dehydration of the resulting alkylguanidine nitrate with nitric acid, removal of excess nitric acid and acid-catalysed reaction of the alkylnitroguanidine obtained with formaldehyde in formic and/or acetic acid. Production of 3-alkyl-N-nitro-4H-1,3,5-oxadiazine-4-imines of formula (I) comprises: (a) neutralization of nitric acid (HNO3) with an alkylamine R-NH2 in aqueous solution at -10 deg C to +50 deg C and optional water removal; (b) reaction of the alkylammonium nitrate obtained with cyanamide in an organic solvent at 80-180 deg C under 2-20 bar pressure; (c) dehydration of the resulting alkylguanidine nitrate (after solvent removal) with 92-98% HNO3 at 20-70 deg C; (d) vacuum distillation of the excess HNO3 at 30-70 deg C; (e) acid-catalysed reaction of the anhydrous alkylnitroguanidine obtained with formic acid in at least 95% formic and/or acetic acid at 30-100 deg C; and (f) isolation of the compound (I) formed. R = 1-4C alkyl.
IPC 1-7
IPC 8 full level
C07D 273/04 (2006.01)
CPC (source: EP)
C07D 273/04 (2013.01)
Citation (search report)
See references of WO 0125222A1
Designated contracting state (EPC)
AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE
DOCDB simple family (publication)
DE 19947332 A1 20010405; EP 1218362 A1 20020703; WO 0125222 A1 20010412
DOCDB simple family (application)
DE 19947332 A 19991001; EP 0009343 W 20000925; EP 00967772 A 20000925