Ammonia → HCID 19782853, compound

HRID 257291Notes

Reaction equation

HRID 257291 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([C:14]2[CH:19]=[CH:18][C:17](O)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=2)([CH3:13])[CH3:12])[CH:7]=[CH:8][C:9]=1O)([O-:3])=[O:2].[Cl-].[NH4+:25].[NH3:26].[OH-].[Na+]>O>[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:26])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=2)([CH3:13])[CH3:12])[CH:7]=[CH:8][C:9]=1[NH2:25])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 2199584,4'-propane-2,2-diylbis(2-nitrophenol)

Product 1

HCID 19782853HCID 19782853, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A typical run consisted of charging the reactor with 35 grams of 2,2-bis(3-nitro-4-hydroxyphenyl)propane, 20 grams of ammonium chloride, 40 ml of water and a stirring bar. The vessel was capped and placed in a -70° C. freezer overnight to freeze the contents. Ammonia was condensed into a 100 ml flask until 63 ml had been collected. The ammonia was added to the reaction vessel and the vessel bolted shut. A variable transformer and heating tape were used to heat the contents to 140° C. for 30 hours and a stirring plate was used to keep the reaction well mixed. The vessel was then allowed to cool to room temperature and vented to release the excess ammonia. The contents were slurried with 500 ml of 1 molar sodium hydroxide solution to dissolve the unreacted starting materials. The slurry was filtered, washed with distilled water, and dried. Recrystallization from toluene and vacuum sublimation gave 32.5 grams (93%) of orange 2,2-bis(3-nitro-4-aminophenyl)propane melting at 207°-210° C. Several runs of the amination reaction were completed to produce enough material for the reduction step. Analysis calculated for C15H16N4O4 : C, 56.96%; H, 5.10%; N, 17.71%; 0, 20.23%. Found: C, 57.06%; H, 5.23%; N, 17.48%; O, 20.28%.

Workup

  1. customThe vessel was capped
  2. customcondensed into a 100 ml flask until 63 ml
  3. customhad been collected
  4. additionThe ammonia was added to the reaction vessel
  5. temperatureA variable transformer and heating tape
  6. customthe reaction
  7. additionwell mixed
  8. temperatureto cool to room temperature
  9. dissolutionto dissolve the
  10. filtrationThe slurry was filtered
  11. washwashed with distilled water
  12. customdried
  13. customRecrystallization from toluene and vacuum sublimation

Sources & evidence

ORD record
ord-5c90b3dbff434344bf51125d06f76276
Source dataset
uspto-grants-1993_11
Patent number
US05262056

Reaction notes

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