Hydrochloric Acid → 1-(2,6-diethylphenyl)3-(N-methoxy-N'-methylamidino)urea hydrochloride

HRID 1733449Notes

Reaction equation

HRID 1733449 reaction equation
C1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[CH3:17][O:18][NH:19][C:20]([NH:22][CH3:23])=[NH:21].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][CH3:42])[C:36]=1[N:43]=[C:44]=[O:45])[CH3:34].[ClH:46]>O1CCCC1.CO>[ClH:46].[CH2:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][CH3:42])[C:36]=1[NH:43][C:44]([NH:21][C:20](=[N:22][CH3:23])[NH:19][O:18][CH3:17])=[O:45])[CH3:34]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 51531832,6-Diethylphenyl isocyanateHCID 178485187HCID 178485187, compound

Product 1

HCID 204652781-(2,6-diethylphenyl)3-(N-methoxy-N'-methylamidino)urea hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 10.0 g. (30.0 mmol) of N-methoxy-N'-methyl guanidine picrate in tetrahydrofuran (60 ml.) are added 2.4 g. (30.0 mmol) of fifty percent (w/w) aqueous sodium hydroxide and the mixture stirred for 11/2 hours. Five (5.0) grams of anhydrous sodium sulfate is added and the mixture stirred for an additiional one-half hour. To this mixture is added a solution of 4.8 g. (30.0 mmol) of 2,6-diethylphenylisocyanate in tetrahydrofura (20 ml.) and the mixture stirred over night. The mixture is partitioned between chloroform and water and the layers are separated. The chloroform layer is washed well with dilute aqueous sodium hydroxide until most of the color is removed then dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil which is dissolved in methanol and acidified with methanolic hydrochloric acid. The ethanol is removed under vacuum to give a gummy foam which is crystallized from methanol/ethyl acetate to give 1-(2,6-diethylphenyl)-3-(N-methoxy-N'-methylamidino)urea hydrochloride, m.p. 159.5°-160.5° C.

Workup

  1. additionTo a suspension of 10.0 g
  2. additionTo this mixture is added a solution of 4.8 g
  3. customThe mixture is partitioned between chloroform and water
  4. customthe layers are separated
  5. washThe chloroform layer is washed well with dilute aqueous sodium hydroxide until most of the color
  6. customis removed
  7. dry with materialthen dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oil which
  11. customThe ethanol is removed under vacuum
  12. customto give a gummy foam which
  13. customis crystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-5cbb873092bf44b78cc30fb60138e1a5
Source dataset
uspto-grants-1980_12
Patent number
US04242340

Reaction notes

Loading…