Hydrochloric Acid → HCID 178468329, compound

HRID 1580469Notes

Reaction equation

HRID 1580469 reaction equation
Cl.[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].[N:13]([O-])=O.[Na+].[CH3:17][C:18](=[O:23])[CH2:19][C:20](=[O:22])[CH3:21].[OH-].[Na+]>O>[F:2][C:3]([F:11])([F:12])[C:4]1[CH:10]=[CH:9][CH:8]=[C:6]([NH:7][N:13]=[C:19]([C:18](=[O:23])[CH3:17])[C:20](=[O:22])[CH3:21])[CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73753-(Trifluoromethyl)anilineHCID 14798Sodium HydroxideHCID 31261AcetylacetoneHCID 23668193Sodium Nitrite

Product 1

HCID 178468329HCID 178468329, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a cold (0° C.) solution of 80 ml. of concentrated hydrochloric acid and 300 ml. of water, there is added a solution of 49.2 g. (0.305 mole) of m-trifluoromethylaniline and then a solution of 22.1 g. (0.32 mole) of sodium nitrite in 100 ml. of water. The resulting benzenediazonium chloride solution is filtered to remove a small amount of insoluble material. To this solution is added 100 g. of sodium acetate followed by a solution of 30.5 g. (0.305 mole) of 2,4-pentanedione and 12.2 g. (0.305 mole) of sodium hydroxide in 150 ml. of water. After about 0.5 hour the solids that form are filtered, washed with water, partly dried on the filter funnel and recrystallized from 450 ml. of ethanol to yield 76.6 g. (92% yield) of product (III), melting at 107.5° to 109° C. An analytical sample is obtained by recrystallization from ethanol to give pure 2,3,4-pentanetrione 3 -[(α,α,α-trifluoro-m-tolyl)hydrazone] (III), melting at 108 to 109.5°C. with slight softening at 102° C.

Workup

  1. customTo a cold (0° C.) solution of 80 ml
  2. filtrationThe resulting benzenediazonium chloride solution is filtered
  3. customto remove a small amount of insoluble material
  4. additionTo this solution is added 100 g
  5. filtrationAfter about 0.5 hour the solids that form are filtered
  6. washwashed with water
  7. custompartly dried on the filter funnel
  8. customrecrystallized from 450 ml
  9. customof ethanol to yield 76.6 g

Sources & evidence

ORD record
ord-f22b14bf3aa34ff7b65cb462bee69aff
Source dataset
uspto-grants-1976_01
Patent number
US03932662

Reaction notes

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