Acetate → 1-Acetoxy-2,4,6-trinitro-2,4,6-triazaheptane

HRID 5222

Reaction equation

HRID 5222 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[N+]([O-])([O-])=O.S([O-])([O-])(=O)=O.[N+]([O-])(O)=O.CC(OC(C)=O)=O.[CH3:25][N:26]([N+:39]([O-:41])=[O:40])[CH2:27][N:28]([N+:36]([O-:38])=[O:37])[CH2:29][N:30]([N+:33]([O-:35])=[O:34])[CH2:31]O.CN1CCC(=C2C3C(=CC=CC=3)C=CC3C2=CC=CC=3)CC1>O.CC(O)=O>[C:1]([O:4][CH2:31][N:30]([N+:33]([O-:35])=[O:34])[CH2:29][N:28]([N+:36]([O-:38])=[O:37])[CH2:27][N:26]([N+:39]([O-:41])=[O:40])[CH3:25])(=[O:3])[CH3:2]

Participants

10

Reactant 7

HCID 175Acetate2×HCID 943NitrateHCID 944Nitric Acid3×HCID 1117Sulfate IonHCID 2913CyproheptadineHCID 7918Acetic Anhydride2×HCID 572623536-Methyl-2,4,6-trinitro-2,4,6-triazahexanol2×

Product 1

HCID 197979901-Acetoxy-2,4,6-trinitro-2,4,6-triazaheptane

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

"Acetate or nitrate of 6-alkyl-2,4,6-trinitro-2,4,6-triazahexanol. Jiri Denkstein and Vladimir Kaderabek. Czech. 98,248, Jan. 15, 1961, Appl. Nov. 13, 1959. The described method is the nitrolysis of N-alkylhexamethylene-tetraminium nitrate, sulfate, or acetate with a mixt. of HNO3 with Ac2O, or anhydride of HNO3. Thus, a mixt. of 30 g N-methylhexamethylenetetraminium nitrate (I) and 49 ml. AcOH added during 15-30 min with stirring at 15°-20° to the mixt. of 52 ml. 98-9% HNO3, and 48 ml. Ac2O under stirring, the temp. increased to 75° and kept 15 min. gave after cooling to 20°-5° 22.2 g cryst. 6-methyl-2,4,6-trinitro-2,4,6-triazahexanol (II). The reactin mixt. dild. with water gave addnl. 5.3 g II. The total yield was 27.5 g of a product, m. 151°-3° , i.e., 68% of theory calcd. on I."

Workup

  1. temperatureincreased to 75°
  2. customgave
  3. temperatureafter cooling to 20°-5° 22.2 g cryst
  4. custom151°-3° , i.e., 68% of theory calcd

Sources & evidence

ORD record
ord-441df664c30c4a9e9bf4d09ba8dd20c5
Source dataset
uspto-grants-1993_09
Patent number
US05243075

Linked notes

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