Hydrochloric Acid → HCID 13550879, compound

HRID 745135Notes

Reaction equation

HRID 745135 reaction equation
C([O:4][CH2:5][CH2:6][C:7]([N+:30]([O-:32])=[O:31])([N+:27]([O-:29])=[O:28])[CH2:8][N:9]([N+:24]([O-:26])=[O:25])[CH2:10][C:11]([N+:21]([O-:23])=[O:22])([N+:18]([O-:20])=[O:19])[CH2:12][CH2:13][O:14]C(=O)C)(=O)C.CO.Cl>O>[N+:30]([C:7]([N+:27]([O-:29])=[O:28])([CH2:8][N:9]([N+:24]([O-:26])=[O:25])[CH2:10][C:11]([N+:18]([O-:20])=[O:19])([N+:21]([O-:23])=[O:22])[CH2:12][CH2:13][OH:14])[CH2:6][CH2:5][OH:4])([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13550878HCID 13550878, compound

Product 1

HCID 13550879HCID 13550879, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crude 3,3,5,7,7-pentanitro-5-azanonane-1,9-diol-1,9-diacetate (66.5 g) was stirred in 615 ml of warm (50° C.) MeOH in a 2000 ml round-bottom flask. Distilled water (265 ml) was added followed by 19 ml of concentrated hydrochloric acid. The mixture was heated at 67°-69° C. (mild reflux) overnight before nearly all the solvent was removed under reduced pressure on a rotary evaporator (water bath at 35° C.). The white solid (mp 118°-120° C.) was removed by filtration and washed with cold water. Crystallization from methanol-water gave 50.0 g, mp 121.5°-123° C. The second crop (2.9 g, mp 118°-120° C.) raised the yield to 52.9 g (97 percent). 1H NMR (acetone-d6 +1 dr. D2O): δ3.00 (t, 2H), 2.90 (t, 2H), 5.57 (s, 2H).

Workup

  1. temperatureThe mixture was heated at 67°-69° C.
  2. temperature(mild reflux) overnight before nearly all the solvent
  3. customwas removed under reduced pressure on a rotary evaporator (water bath at 35° C.)
  4. customThe white solid (mp 118°-120° C.) was removed by filtration
  5. washwashed with cold water
  6. customCrystallization from methanol-water
  7. customgave 50.0 g, mp 121.5°-123° C
  8. temperatureThe second crop (2.9 g, mp 118°-120° C.) raised the
  9. customyield to 52.9 g (97 percent)

Sources & evidence

ORD record
ord-f98fbb86834a4ac68ba91db900c1f854
Source dataset
uspto-grants-1986_07
Patent number
USH0000078

Reaction notes

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