Sulfuric Acid → HCID 20289727, compound

HRID 27210Notes

Reaction equation

HRID 27210 reaction equation
[CH:1](=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:6][C:7]([NH2:9])=[O:8].S(=O)(=O)(O)O.[OH-].[Na+]>O.C1(C)C(C)=CC=CC=1>[NH2:6][C:7]([NH2:9])=[O:8].[CH:1](=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 6561IsobutyraldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 20289727HCID 20289727, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
60 °C

Procedure

864 Parts of isobutyraldehyde, 800 parts of xylene and 240 parts of urea are mixed, and heated to the boil, in a stirred flask equipped with a condenser, water separator, thermometer and dropping funnel. 50 Parts of 75% strength sulfuric acid are added dropwise in the course of about 10 minutes and the mixture is then stirred for 5 hours at the boil. The resulting water (158 parts) is removed via the water separator. During the condensation reaction, the temperature rises to 123°-125° C. The mixture is then cooled to 80° C. and neutralized with about 50 parts of 50% strength sodium hydroxide solution, and further water is removed at the boil until the temperature reaches 132°-135° C. 60 Parts of 30% strength sodium methylate solution in methanol are then added to the contents of the flask, which are stirred for 1 hour at the boil (112°-115° C.). The mixture is then cooled to 60° C., neutralized with 75% strength sulfuric acid and washed with 1,000 parts of water at 80° C. After separating off the wash water, the solvent is distilled from the xylene phase under reduced pressure (20-25 mm Hg), the temperature in the flask being 175° C.

Workup

  1. temperatureheated to the boil, in a stirred flask
  2. customequipped with a condenser
  3. customThe resulting water (158 parts) is removed via the water separator
  4. customDuring the condensation reaction
  5. customrises to 123°-125° C
  6. customis removed at the boil until the temperature
  7. customreaches 132°-135° C
  8. addition60 Parts of 30% strength sodium methylate solution in methanol are then added to the contents of the flask, which
  9. stirringare stirred for 1 hour at the boil (112°-115° C.)
  10. washwashed with 1,000 parts of water at 80° C
  11. customAfter separating off the wash water
  12. distillationthe solvent is distilled from the xylene phase under reduced pressure (20-25 mm Hg)
  13. custombeing 175° C.

Sources & evidence

ORD record
ord-aeb4b2adb1b943e8b5343310512f19f2
Source dataset
uspto-grants-1980_09
Patent number
US04220751

Reaction notes

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