Sodium Hydroxide → 1-(1,3-Benzodioxol-5-yl)-1-isopropylurea

HRID 1973431Notes

Reaction equation

HRID 1973431 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH2:12][O:13][C:7]=2[CH:6]=1)([CH3:3])[CH3:2].[N-:14]=[C:15]=[O:16].[Na+].[OH-].[Na+]>C(O)(=O)C>[CH:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH2:12][O:13][C:7]=2[CH:6]=1)[C:15]([NH2:14])=[O:16])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11051568NaNCOHCID 12789466N-(Propan-2-yl)-2H-1,3-benzodioxol-5-amine

Product 1

HCID 1005551-(1,3-Benzodioxol-5-yl)-1-isopropylurea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 14.7 gm. of N-isopropyl-3,4-methylenedioxyaniline, prepared as in Example A, in 200 ml. of glacial acetic acid, cooled to 10°-18°C., is added 4.9 gm. of sodium isocyanate (sodium cyanate) in several portions. The resulting mixture is then stirred at ambient temperature for 15 hours. At the end of this time, the solvent is stripped at reduced pressure and the solid residue treated with 300 ml. of 2N sodium hydroxide. The resulting mixture is extracted with chloroform, dried and evaporated. The gum thus obtained is recrystallized from cyclohexane to obtain N-isopropyl-N-(3,4-methylenedioxyphenyl)urea, m.p. 116°-119°C.

Workup

  1. additionis added 4.9 gm
  2. additionthe solid residue treated with 300 ml
  3. extractionThe resulting mixture is extracted with chloroform
  4. customdried
  5. customevaporated
  6. customThe gum thus obtained
  7. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-19a415d1e1514a3a9c8c6864e05ef80b
Source dataset
uspto-grants-1976_12
Patent number
US03997564

Reaction notes

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