Sulfuric Acid → HCID 19357420, compound

HRID 377126Notes

Reaction equation

HRID 377126 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[NH:13][CH2:14][CH2:15][NH:16][C:17]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:18]=1[N+:26]([O-])=O)([O-])=O.[H][H].[S:31](=[O:35])(=[O:34])([OH:33])[OH:32]>[Pd].CO>[S:31]([OH:35])([OH:34])(=[O:33])=[O:32].[NH2:26][C:18]1[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:17]=1[NH:16][CH2:15][CH2:14][NH:13][C:5]1[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 19357424HCID 19357424, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19357420HCID 19357420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

150 ml of methanol were introduced into a 0.3 liter autoclave, 16.7 g (0.2 mole) of N,N'-bis-(2,5-dinitrophenyl)-1,2-diaminoethane were dissolved therein and 2 g of palladium on active carbon 10% (Degussa) were added. After the autoclave had been closed and blanketed with nitrogen, hydrogenation was carried out under a pressure of 3 bar and at a temperature of 35 to 40° C. until no more hydrogen was taken up. The mixture was emptied onto a pressure filter, the residue was dissolved in 100 ml of N-methyl pyrrolidone at 100° C., the catalyst was filtered off using a pressure filter and, after cooing of the filtrate to 5-10° C., 9.8 g (0.1 mole) of 80% sulfuric acid were added dropwise. The jelly-like precipitate was stirred with 200 ml of methanol. The crystallized product was filtered off under suction, washed with methanol and dried.

Workup

  1. dissolutionwere dissolved
  2. customAfter the autoclave had been closed
  3. filtrationfilter
  4. dissolutionthe residue was dissolved in 100 ml of N-methyl pyrrolidone at 100° C.
  5. filtrationthe catalyst was filtered off
  6. filtrationfilter
  7. customafter cooing of the filtrate to 5-10° C.
  8. filtrationThe crystallized product was filtered off under suction
  9. washwashed with methanol
  10. customdried

Sources & evidence

ORD record
ord-449cd3ec0bff457fbbb231f531cb14de
Source dataset
uspto-grants-2000_02
Patent number
US06024768

Reaction notes

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