Benzocaine → HCID 136331486, compound

HRID 1587741Notes

Reaction equation

HRID 1587741 reaction equation
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.C([O-])([O-])[O:14][CH2:15][CH3:16].[CH3:19][N:20]1CCN(C)C1=O.[N+:27]([N:30]=[C:31]1[NH:35][CH2:34][CH2:33][NH:32]1)([O-:29])=[O:28]>C(OCC)(=O)C>[CH2:15]([O:14][C:3]1[CH:2]=[CH:12][CH:11]([N:20]=[CH:19][N:32]2[CH2:33][CH2:34][NH:35][C:31]2=[N:30][N+:27]([O-:29])=[O:28])[C:5](=[C:6]=[O:8])[CH:4]=1)[CH3:16]

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 53630039EthylorthoformateHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 136331486HCID 136331486, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 10.0 g of ethyl p-aminobenzoate, 10.8 g of ethyl orthoformate, 10 ml of 1,3-dimethyl-2-imidazolidinone and 0.05 g of boron trifluoride ether complex was placed in a reactor equipped with Dean's stark tube and agitated at 140° C. for about 5 minutes, followed by further addition of 7.9 g of nitroiminoimidazolidine and agitation at 180° C. for 1 hour. The reaction mixture was poured into 200 ml of a saturated saline solution, to which 150 ml of ethyl acetate was added. The resultant crystals were collected by filtration and dried to give 12.3 g of 1-(4-ethoxy-carbonylphenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. customwas placed in a reactor
  2. customequipped with Dean's stark tube
  3. additionwas added
  4. filtrationThe resultant crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-d704c87f90d0409d95b575ef0e448e32
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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