Nitric Acid → HCID 13550878, compound

HRID 745134Notes

Reaction equation

HRID 745134 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-])([OH:10])=[O:9].[C:12]([O:15][CH2:16][CH2:17][C:18]([N+:38]([O-:40])=[O:39])([N+:35]([O-:37])=[O:36])[CH2:19][NH:20][CH2:21][C:22]([N+:32]([O-:34])=[O:33])([N+:29]([O-:31])=[O:30])[CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])(=[O:14])[CH3:13]>>[C:26]([O:25][CH2:24][CH2:23][C:22]([N+:32]([O-:34])=[O:33])([N+:29]([O-:31])=[O:30])[CH2:21][N:20]([N+:8]([O-:10])=[O:9])[CH2:19][C:18]([N+:38]([O-:40])=[O:39])([N+:35]([O-:37])=[O:36])[CH2:17][CH2:16][O:15][C:12](=[O:14])[CH3:13])(=[O:28])[CH3:27]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 13550877HCID 13550877, compound

Product 1

HCID 13550878HCID 13550878, compound

Procedure

Acetic anhydride (315 ml) was stirred in an ice bath to maintain a temperature of 20°-23° C. during the slow addition of 95 ml of 90 percent nitric acid. The solution was then cooled to 5° C. while 3,3,7,7-tetranitro-5-azanonane-1,9-diol-1,9-diacetate was added in portions with good stirring. The solution was stirred at ambient temperature overnight before it was poured into ice water. The mixture was stirred for one hour and the solid (66.5 g, 97 percent, mp 87°-89° C.) was removed by filtration. A recrystallized sample (CH2Cl2 /hexane) had mp 88°-89° C.; 1H NMR (CDCl3): δ2.09 (s, 3H), 3.00 (t, 2H), 4.35 (t, 2H), 5.20 (s, 2H).

Workup

  1. temperatureto maintain a temperature of 20°-23° C.
  2. additionwas added in portions with good stirring
  3. stirringThe mixture was stirred for one hour
  4. customthe solid (66.5 g, 97 percent, mp 87°-89° C.) was removed by filtration

Sources & evidence

ORD record
ord-cc9d700d42194b11acaa4b519fc40331
Source dataset
uspto-grants-1986_07
Patent number
USH0000078

Reaction notes

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