Hydrochloric Acid → HCID 59824348, compound

HRID 1845705Notes

Reaction equation

HRID 1845705 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=3[CH3:26])[C:13](=[O:27])[N:12]([C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][C:29]=3[CH3:37])[C:11]2=[O:38])=[C:6]([CH3:39])[CH:5]=1)([O-])=O.Cl.O>C1COCC1.[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[C:15](=[O:16])[N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][C:6]=3[CH3:39])[C:11](=[O:38])[N:12]([C:28]3[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][C:29]=3[CH3:37])[C:13]2=[O:27])=[C:18]([CH3:26])[CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59847714HCID 59847714, compound

Product 1

HCID 59824348HCID 59824348, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1,3,5-tris-(4-nitro-2-methyl-phenyl)-[1,3,5]triazinane-2,4,6-trione (2.86 g, 5.4 mmol) was dissolved in THF (70 ml). HCl (4.5 ml, 6M), water (18 ml) and Pd/C (0.6 g, 10%) was added. The reaction vessel was evacuated and filled with argon in three cycles before hydrogenated on a Parr hydrogenation apparatus (60 psi). After 2 hours the excess hydrogen was evacuated with a membrane pump and the Pd/C (10%) was filtered off. The clear reaction solution was concentrated until no more THF remained and the pH adjusted to 7 with NaHCO3 (˜3.7 g). The aqueous phase was extracted with ethyl acetate (3×100 ml) and the combined organic phases were dried with MgSO4, filtered and concentrated to give a brown powder. The crude product was recrystallized from methanol to give the product as an off-white powder (1.9 g, 80%).

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with argon in three cycles before hydrogenated on a Parr hydrogenation apparatus (60 psi)
  3. customAfter 2 hours the excess hydrogen was evacuated with a membrane pump
  4. filtrationthe Pd/C (10%) was filtered off
  5. concentrationThe clear reaction solution was concentrated until no more THF
  6. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  7. dry with materialthe combined organic phases were dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a brown powder
  11. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-f129506c0413424eac50b83a617e6ed2
Source dataset
uspto-grants-2015_02
Patent number
US08951502B2

Reaction notes

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