Sulfuric Acid → HCID 10307918, compound

HRID 2194933Notes

Reaction equation

HRID 2194933 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.[N+]([O-])(O)=O.N[C:19]([NH2:21])=O.[C:22]([O:25]CC)(=[O:24])C.[CH3:28]CCCCC>[OH-].[Na+]>[NH:6]1[C:7]2[C:12](=[CH:11][C:10]([CH:13]([CH3:28])[C:22]([OH:25])=[O:24])=[CH:9][CH:8]=2)[CH:19]=[N:21]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7813p-ToluidineHCID 31295Carbamimidic acid--nitric acid (1/1)HCID 21226206Ethyl acetate hexane

Product 1

HCID 10307918HCID 10307918, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Sulfuric acid (365.8 g, 3.73 mol, 10 eq) was added drop wise to p-toluidine (40 g, 0.37 mol) at it and stirred the contents to obtain a clear solution. Then Urea nitrate (45.5 g, 0.37 mol, 1 eq) was added at 0-10° C. and stirred the reaction mass for 30 min at the same temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane, Rf˜0.5). On completion of the reaction, reaction mixture was quenched with ice water and the solid formed was filtered. Solid obtained was taken in 20% NaOH solution (up to pH˜12) and filtered. Washed the solid and dried to yield the required product as an yellow colored solid (50 g, 88% yield).

Workup

  1. customto obtain a clear solution
  2. stirringstirred the reaction mass for 30 min at the same temperature
  3. customOn completion of the reaction, reaction mixture
  4. customwas quenched with ice water
  5. customthe solid formed
  6. filtrationwas filtered
  7. customSolid obtained
  8. filtrationfiltered
  9. washWashed the solid
  10. customdried

Sources & evidence

ORD record
ord-df32e1563be546e3934f070a7db93dec
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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