HCID 178512769, compound → HCID 178512767, compound

HRID 1731487Notes

Reaction equation

HRID 1731487 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[N+:6]([C:9]1[CH:19]=[CH:18][C:12]([CH2:13][NH:14][C:15]([NH2:17])=[NH:16])=[CH:11][CH:10]=1)([O-])=O>O.[Ni]>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH2:6][C:9]1[CH:19]=[CH:18][C:12]([CH2:13][NH:14][C:15]([NH2:17])=[NH:16])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 178512769HCID 178512769, compound

Product 1

HCID 178512767HCID 178512767, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

4-Nitrobenzylguanidine sulfate (0.243 g, 1.0 mmol) was dissolved in water (50 ml) by gentle warming and then cooled to ambient temperature. Activated Raney-Nickel catalyst (Wet form, Aldrich Chemical Co.) (500 mg) was added and the mixture was hydrogenated at 50 p.s.i. for 90 min. The catalyst was filtered and washed with water. To the clear, colorless filtrate was added 2N H2SO4 to pH 1.5. The solution was concentrated to approximately 25 ml; 95% ethanol (150 ml) was added and the solution stored at 4° C. overnight. The colorless needles were filtered and recrystallized from 1N H2SO4 (8 ml) to give stout prisms (0.205 g, 78%), m.p. 248°-250° C. (dec); IR (cm-1) Nujol 3395 (NH), 3260 (NH), 1675 and 1655 (C=N), 1060 (S=O) 835 (1,4 disubstituted benzene); PMR (DMSO-d6) 7.52 (t, 1H, J=5 Hz, CH2NH--), 6.90 (m, 7H) 6.40 (d, 2H, J=8.5 Hz) and 3.98 (d, 2H, J=5 Hz, CH2NH). Anal. calcd. for C8H12N4.H2SO4 : C, 36.64; H, 5.34; N, 21.37. Found: C, 36.70; H, 5.30; N, 21.39.

Workup

  1. temperatureby gentle warming
  2. filtrationThe catalyst was filtered
  3. washwashed with water
  4. additionTo the clear, colorless filtrate was added 2N H2SO4 to pH 1.5
  5. concentrationThe solution was concentrated to approximately 25 ml
  6. addition95% ethanol (150 ml) was added
  7. waitthe solution stored at 4° C. overnight
  8. filtrationThe colorless needles were filtered
  9. customrecrystallized from 1N H2SO4 (8 ml)

Sources & evidence

ORD record
ord-e86f0d200ca54808ad11da5f59cf68fd
Source dataset
uspto-grants-1986_11
Patent number
US04622217

Reaction notes

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