Hydrochloric Acid → 1-(2,6-Dimethylphenyl)-3-(1,2-oxazolidine-2-carboximidoyl)urea;hydrochloride

HRID 325529Notes

Reaction equation

HRID 325529 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[C:8]([N:11]1[CH2:15][CH2:14][CH2:13][O:12]1)(=[NH:10])[NH2:9].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[N:31]=[C:32]=[O:33].[N-]=C=O.[ClH:37]>O1CCCC1.CO.C(OCC)(=O)C>[ClH:37].[CH3:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH3:23])[C:25]=1[NH:31][C:32]([NH:10][C:8]([N:11]1[CH2:15][CH2:14][CH2:13][O:12]1)=[NH:9])=[O:33]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 987872,6-Xylyl isocyanateHCID 105034IsocyanateHCID 20465274N-amidinoisooxazolidine sulfate

Product 1

HCID 1457970781-(2,6-Dimethylphenyl)-3-(1,2-oxazolidine-2-carboximidoyl)urea;hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 2.9 g. (36.0 mmol) of fifty percent (w/w) sodium hydroxide suspended in tetrahydrofuran (50 ml.) is added 6.0 g. (18.0 mmol) of N-amidinoisooxazolidine sulfate and the mixture stirred for one hour. Five (5.0) grams of anhydrous sodium sulfate are added and the mixture stirred for an additional hour. To this mixture are added 5.4 g. (36.0 mmol) of 2,6-dimethylphenylisocyanate and the mixture stirred for three hours. Thin layer chromotography (ethyl acetate) showed no starting isocyanate so the tetrahydrofuran is removed under vacuum. The residue is partitioned between water and chloroform. The layers are separated and the aqueous layer extracted with chloroform (1×100 ml.). The combined chloroform extracts are dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil which is dissolved in methanol and acidified (pH=1) with methanolic hydrochloric acid. The methanol is removed to give an oil which is triturated with diethyl ether to give a solid which is crystallized from tetrahydrofuran/hexane to give N-[(2,6-dimethylphenylcarbamoyl)amidino]isooxazolidine hydrochloride, m.p. 147°-8° C.

Workup

  1. additionis added 6.0 g
  2. additionTo this mixture are added 5.4 g
  3. customis removed under vacuum
  4. customThe residue is 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 chloroform extracts are dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oil which
  11. customThe methanol is removed
  12. customto give an oil which
  13. customis triturated with diethyl ether
  14. customto give a solid which
  15. customis crystallized from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-32056b6f399a422992ef8bfc75d8bea8
Source dataset
uspto-grants-1984_04
Patent number
US04440949

Reaction notes

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