Aniline → HCID 12876082, compound

HRID 1757955Notes

Reaction equation

HRID 1757955 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][N:9]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[C:10](Cl)=[O:11]>O1CCCC1>[CH3:16][N:15]([CH3:17])[C:13]([N:9]([CH3:8])[C:10]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11])=[O:14]

Participants

4

Reactant 2

HCID 6115AnilineHCID 11062732HCID 11062732, compound

Product 1

HCID 12876082HCID 12876082, compoundYield 146.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of anhydrous tetrahydrofuran, 7.4 g (0.08 mole) of aniline was dissolved. The mixture was cooled below 0° C., and a solution prepared by dissolving 6.4 g (0.04 mole) of 2,4,4-trimethylallophanoyl chloride in 10 ml of anhydrous tetrahydrofuran was added dropwise under stirring. The reaction was continued at a room temperature for 1 hour, then the solvent was removed by distillation under a reduced pressure, and water was added to form an insoluble matter. The insoluble matter was obtained by filtration and was recrystallized from ethanol to obtain 13.0 g (yield 73%) of 1,1,3-trimethyl-5-phenylbiuret having a melting point 89.5°-90.5° C.

Workup

  1. temperatureThe mixture was cooled below 0° C.
  2. customa solution prepared
  3. additionwas added dropwise
  4. customthe solvent was removed by distillation under a reduced pressure, and water
  5. additionwas added
  6. customto form an insoluble matter
  7. customThe insoluble matter was obtained by filtration
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-43bb54102b8745658bbd662d73efda79
Source dataset
uspto-grants-1983_02
Patent number
US04371544

Reaction notes

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