Acetic Acid → HCID 178514356, compound

HRID 2398036Notes

Reaction equation

HRID 2398036 reaction equation
CO[C:3](=[O:16])[C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[C:7]([Cl:12])=[C:6]([Cl:13])[C:5]=1[C:14]#[N:15].O.[NH2:18][NH2:19].C(O)(=O)C>CO>[Cl:13][C:6]1[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]([Cl:10])=[C:4]2[C:5]=1[C:14](=[N:18][NH2:19])[NH:15][C:3]2=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 79319Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester

Product 1

HCID 178514356HCID 178514356, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

119.6 g of 3,4,5,6-tetrachloro-2-cyanobenzoic acid methyl ester are dissolved in 600 ml of methanol and 70.6 g of a 30.6% strength methanolic solution of Na methylate. The solution is cooled to 10° C and is added dropwise at 10° C to a solution of 200 ml of hydrazine hydrate in 400 ml of methanol. A yellowish precipitate is formed. The reaction mixture is stirred at room temperature for 2 hours and is then warmed to 35° C over the course of 30 minutes and 200 ml of glacial acetic acid are added at this temperature. After stirring for 1 hour at room temperature, the product is filtered off and the filter residue is washed with methanol and water. The material filtered off is then extracted by boiling in 1 l of methylcellosolve for a further 2 hours, filtered off at room temperature and washed with methylcellosolve and methanol. After drying at 70° C, 98 g (82% of theory) of analytically pure 4,5,6,7-tetrachloro-isoindolin-1-on- 3-ylidene hydrazine of the formula ##STR31## are obtained.

Workup

  1. customA yellowish precipitate is formed
  2. additionare added at this temperature
  3. stirringAfter stirring for 1 hour at room temperature
  4. filtrationthe product is filtered off
  5. washthe filter residue is washed with methanol and water
  6. filtrationThe material filtered off
  7. extractionis then extracted
  8. waitby boiling in 1 l of methylcellosolve for a further 2 hours
  9. filtrationfiltered off at room temperature
  10. washwashed with methylcellosolve and methanol
  11. customAfter drying at 70° C

Sources & evidence

ORD record
ord-34181bef555a4d9e8f47172bd2174b93
Source dataset
uspto-grants-1977_05
Patent number
US04024132

Reaction notes

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