Hydrochloric Acid → 2-(4-Isopropoxy-2-fluorophenyl)hydrazonomalonyldiurethane

HRID 257379

Reaction equation

HRID 257379 reaction equation
[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([F:12])[CH:6]=1)([CH3:3])[CH3:2].[C:13]([NH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:23])[CH2:14][C:15]([NH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16].C([O-])(=O)C.[Na+].Cl.[N:36]([O-])=O.[Na+]>O>[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][N:36]=[C:28]([CH3:29])[O:27][C:25](=[O:26])[NH:24][C:13](=[O:23])[CH2:14][C:15]([NH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[C:7]([F:12])[CH:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 154305Carbamic acid, (1,3-dioxo-1,3-propanediyl)bis-, diethyl esterHCID 517045Sodium AcetateHCID 37563842-Fluoro-4-isopropoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 676305712-(4-Isopropoxy-2-fluorophenyl)hydrazonomalonyldiurethaneYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

A mixture of 5.92 g (0.035 mole) of 4-isopropoxy-2-fluoroaniline, 10.60 g (0.043 mole) of malonyldiurethane, and 41.02 g (0.500 mole) of sodium acetate was suspended in 1000 mL of water with vigorous stirring. To this suspension was added 25 mL of 12N hydrochloric acid. The reaction mixture was cooled to 10° C., and, while this temperature was maintained, a solution of 2.42 g (0.035 mole) of sodium nitrite in 25 mL of water was slowly added. The reaction mixture was allowed to warm slowly to room temperature where it was stirred under a nitrogen atmosphere for approximately 16 hours. During this period a yellow solid formed and precipitated out. The mixture was filtered, and the yellow solid was washed in succession with water and diethyl ether. After being dried, 9.20 g of 2-(4-isopropoxy-2-fluorophenyl)hydrazonomalonyldiurethane was isolated as a yellow solid. The NMR and IR spectra were consistent with the proposed structure.

Workup

  1. temperaturewhile this temperature was maintained
  2. temperatureto warm slowly to room temperature where it
  3. customDuring this period a yellow solid formed
  4. customprecipitated out
  5. filtrationThe mixture was filtered
  6. washthe yellow solid was washed in succession with water and diethyl ether
  7. customAfter being dried

Sources & evidence

ORD record
ord-716d7a9a96734e9d80a99e2ba66e8f0e
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Linked notes

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