Sodium Hydroxide → HCID 178436841, compound

HRID 26025Notes

Reaction equation

HRID 26025 reaction equation
S(O)(O)(=O)=O.[CH3:6][NH:7][C:8]([NH2:10])=[NH:9].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:20]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24]([CH2:31][CH3:32])[C:23]=1[N:33]=[C:34]=[O:35])[CH3:21].[ClH:36].CO>O1CCCC1.O.CO>[ClH:36].[CH2:20]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24]([CH2:31][CH3:32])[C:23]=1[NH:33][C:34]([NH:10][C:8](=[NH:9])[NH:7][CH3:6])=[O:35])[CH3:21]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 203836312,6-Diethyl-4-nitrophenylisocyanateHCID 21893726Hydrochloride methanolHCID 178485188HCID 178485188, compound

Product 1

HCID 178436841HCID 178436841, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 7.3 g (30.0 mmol) of methylguanidine sulfate in tetrahydrofuran (80 ml) is added 4.8 g (60.0 mmol) of 50% w/w sodium hydroxide in water with continued stirring for one hour. Anhydrous sodium sulfate (10.0 g) is added and the mixture stirred an additional hour after which 6.6 g (30.0 mmol) of 2,6-diethyl-4-nitrophenylisocyanate is added and the resulting mixture stirred at room temperature over-night. The tetrahydrofuran is removed under vacuum and the residue partitioned between water and chloroform. The layers are separated and the aqueous layer extracted with chloroform (1 × 100 ml). The combined extracts are dried (MgSO4) and concentrated to give a yellow foam which is dissolved in methanol and acidified with HCl/MeOH. The methanol is removed under vacuum to give a yellow viscous oil which solidifies on scratching. Crystallization from methanol-ethyl acetate gives 1-(2,6-diethyl-4-nitrophenyl)-3-methylamidinourea hydrochloride as a pale yellow solid, m.p. 173°-175° C.

Workup

  1. additionis added
  2. stirringthe resulting mixture stirred at room temperature over-night
  3. customThe tetrahydrofuran is removed under vacuum
  4. customthe residue partitioned between water and chloroform
  5. customThe layers are separated
  6. extractionthe aqueous layer extracted with chloroform (1 × 100 ml)
  7. dry with materialThe combined extracts are dried (MgSO4)
  8. concentrationconcentrated
  9. customto give a yellow foam which
  10. customThe methanol is removed under vacuum
  11. customto give a yellow viscous oil which
  12. customCrystallization from methanol-ethyl acetate

Sources & evidence

ORD record
ord-328eb0e795b2461abdd4d2bc8141f4f8
Source dataset
uspto-grants-1979_04
Patent number
US04147804

Reaction notes

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