Sodium Hydroxide → HCID 178502885, compound

HRID 1733474Notes

Reaction equation

HRID 1733474 reaction equation
[ClH:1].[CH3:2][O:3][NH:4][C:5]([NH2:7])=[NH:6].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[N:25]=[C:26]=[O:27]>O1CCCC1>[ClH:1].[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[C:19]=1[NH:25][C:26]([NH:6][C:5](=[NH:7])[NH:4][O:3][CH3:2])=[O:27]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 987872,6-Xylyl isocyanateHCID 178502882HCID 178502882, compound

Product 1

HCID 178502885HCID 178502885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 12.0 g. (0.11 mole) of methoxyguanidine hydrochloride in tetrahydrofuran (100 ml.) is added 8.8 g. (0.11 mole) of fifty percent (w/w) aqueous sodium hydroxide. After one hour of stirring, 5.0 g. of anhydrous sodium sulfate is added and the mixture is stirred for an additional hour. A solution of 14.7 g. (0.1 mole) of 2,6-dimethylphenylisocyanate in tetrahydrofuran (30 ml.) is added dropwise after which the mixture is stirred at room temperature overnight. 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 (4×100 ml.). The combined organic extracts are washed with water (1×50 ml.) dried over anhydrous magnesium sulfate and filtered. The filtrate is acidified with ethereal HCl and the solvents removed in vacuo to give a brown oil which is crystallized from acetonitrile to give 1-(2,6-dimethylphenyl)-3-methoxyamidinourea hydrochloride, m.p. 170°-1° C.

Workup

  1. additionTo a suspension of 12.0 g
  2. stirringthe mixture is stirred for an additional hour
  3. stirringis stirred at room temperature overnight
  4. customThe tetrahydrofuran is removed under vacuum
  5. customthe residue partitioned between water and chloroform
  6. customThe layers are separated
  7. extractionthe aqueous layer extracted with chloroform (4×100 ml.)
  8. washThe combined organic extracts are washed with water (1×50 ml.)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe solvents removed in vacuo
  12. customto give a brown oil which
  13. customis crystallized from acetonitrile

Sources & evidence

ORD record
ord-88063f680c1f4724aafbba9c39d0c54f
Source dataset
uspto-grants-1980_12
Patent number
US04242338

Reaction notes

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