Urea → 1-(p-Tolyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 10385Notes

Reaction equation

HRID 10385 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=O)[CH2:10][CH:9]2[C:11](O)=[O:12])=[CH:4][CH:3]=1.[NH2:17]C(N)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:10][CH:9]2[C:11](=[O:12])[NH:17][C:14]3=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 127197941,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)-

Product 1

HCID 127198301-(p-Tolyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of purified 1-(4-methylphenyl)-1,2-cyclopropanedicarboxylic acid (58 kg), toluene (465 kg) and urea (23.8 kg) was heated to reflux and the mixture held at reflux until the reaction was complete. On completion of the reaction period, the solution was cooled to 80–90° C. and washed with water (69 L). The lower aqueous layer was discarded. In this way (±)-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexan-2,4-dione was obtained as a solution in toluene.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureat reflux until the reaction
  4. customOn completion of the reaction period
  5. temperaturethe solution was cooled to 80–90° C.
  6. washwashed with water (69 L)

Sources & evidence

ORD record
ord-1a5375979fb5402d8fe980b291f4b317
Source dataset
uspto-grants-2006_08
Patent number
US07094799B2

Reaction notes

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