Nitric Acid → HCID 178485172, compound

HRID 26018Notes

Reaction equation

HRID 26018 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+].[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[N:28]([CH3:32])[C:29](Cl)=[O:30].[N+:33]([O-:36])([OH:35])=[O:34]>O1CCCC1>[N+:33]([O-:36])([OH:35])=[O:34].[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[N:28]([CH3:32])[C:29]([NH:10][C:8](=[NH:9])[NH:7][CH3:6])=[O:30]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 20383505HCID 20383505, compoundHCID 178485188HCID 178485188, compound

Product 1

HCID 178485172HCID 178485172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 12.21 g. (0.05 moles) of methyl guanidine sulfate in 110 ml. of tetrahydrofuran is added 8.0 g. (0.10 moles of sodium hydroxide) of 50% aqueous sodium hydroxide. After stirring for 11/2 hours, 4.5 g. of sodium sulfate is slowly added and the mixture stirred an additional 1/2 hour. To the solution is added a solution of 9.88 g. (0.05 moles) of 2,6-dimethylphenyl-N-methylcarbamoyl chloride in 30 ml. of tetrahydrofuran. After stirring for 24 hours, the THF is removed in vacuo and the residue partitioned with chloroform/water. The oily residue is triturated with 300 ml. of hexane and 20 ml. benzene to give a white solid. This is dissolved in 50 ml. of 1:4 HNO3 and warmed slightly over 1/2 hour, then cooled. The white solid which forms is filtered and air dried to obtain 1-(2',6'-dimethylphenyl)-1-methyl-3-methylamidinourea nitrate.

Workup

  1. additionTo a suspension of 12.21 g
  2. stirringthe mixture stirred an additional 1/2 hour
  3. additionTo the solution is added a solution of 9.88 g
  4. stirringAfter stirring for 24 hours
  5. customthe THF is removed in vacuo
  6. customthe residue partitioned with chloroform/water
  7. customThe oily residue is triturated with 300 ml
  8. custombenzene to give a white solid
  9. dissolutionThis is dissolved in 50 ml
  10. temperaturecooled
  11. filtrationThe white solid which forms is filtered
  12. customair dried

Sources & evidence

ORD record
ord-87e20e5127b94517aacddcda20ba5ec1
Source dataset
uspto-grants-1979_04
Patent number
US04147804

Reaction notes

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