Urea → HCID 14068922, compound

HRID 1904780Notes

Reaction equation

HRID 1904780 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:16]([OH:18])=O)[CH2:12][CH:11]2[C:13](O)=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:19]C(N)=O>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]23[CH2:12][CH:11]2[C:13](=[O:14])[NH:19][C:16]3=[O:18])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1176UreaHCID 14068955HCID 14068955, compound

Product 1

HCID 14068922HCID 14068922, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 9.8 g of 1-(3-nitrophenyl)-1,2-cyclopropanedicarboxylic acid and 4.9 g of urea in 250 ml of xylene (mixture of isomers) is stirred for about 16 hours at a bath temperature of about 150° C. The xylene is then evaporated off in vacuo and the residue is partitioned between ethyl acetate and water. The organic phases are combined, dried over MgSO4, filtered, and concentrated in vacuo. Recrystallisation from ethyl acetate/petroleum ether gives the title compound (e) in the form of pale yellow crystals with m.p. 173°-174° C. and Rf=0.3 on thin-layer silica gel plates in the system hexane/ethyl acetate (4:6).

Workup

  1. customThe xylene is then evaporated off in vacuo
  2. customthe residue is partitioned between ethyl acetate and water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-0f562f6ed9194eeaa2d90f7f96525bad
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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