Sodium Carbonate → HCID 85923302, compound

HRID 972872Notes

Reaction equation

HRID 972872 reaction equation
C1(O[C:8]([N:10]2[CH2:14][CH2:13][N:12](C)[C:11]2=[C:16]([N+:26]([O-:28])=[O:27])[C:17](=[O:25])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O.O>[C:19]1([O:18][C:17](=[O:25])[C:16](=[C:11]2[NH:12][CH2:13][CH2:14][N:10]2[CH3:8])[N+:26]([O-:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54201183HCID 54201183, compound

Product 1

HCID 85923302HCID 85923302, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of 15.66 g of phenyl chloroformate in 25 ml of methylene chloride was added to a stirred and ice-cooled solution of 8.21 g of 1-methylimidazole in 175 ml of methylene chloride. To the resulting white suspension was added 7.15 g of 1-methyl-2-(nitromethylene)imidazolidine in portions as a solid. After stirring overnight at room temperature, the reaction mixture was washed twice with water. The organic layer was dried (MgSO4) and concentrated. The residual orange syrup was treated with water, and this mixture allowed to stand at room temperature overnight. The resulting solid was isolated by filtration. Trituration with ethyl acetate gave white powder. Recrystallization from a mixture of 60 ml of dimethyl sulfoxide and 45 ml of water gave 3-methyl-2-(1-nitro-2-oxo-2-phenoxyethylidene)-1-imidazolidinecarboxylic acid phenyl ester (1A), as a white solid, m.p.: 214°-215° C. A heterogeneous mixture of 1.92 g of 1A in 10 ml of dimethyl sulfoxide and 0.55 g of sodium carbonate in 3 ml of water was stirred at room temperature for two days. Crude, solid product was obtained by dilution with 30 ml of water and then filtration. Recrystallization from dimethyl sulfoxide: water yielded 1, as white crystals, m.p.: 234°.

Workup

  1. filtrationfiltration
  2. customRecrystallization from dimethyl sulfoxide
  3. customwater yielded 1

Sources & evidence

ORD record
ord-aa988b820e4a45758685956251b2af5f
Source dataset
uspto-grants-1977_10
Patent number
US04053623

Reaction notes

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