Potassium Carbonate → 3,5-Dimethyl-benzoic acid N-tert-butyl-N'-(4-ethyl-2-fluoro-benzoyl)-hydrazide

HRID 39629Notes

Reaction equation

HRID 39629 reaction equation
[C:1]([N:5]([C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)[NH2:6])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:26]=[C:25]([CH2:27][CH3:28])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[C:1]([N:5]([C:7](=[O:16])[C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1)[NH:6][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:25]([CH2:27][CH3:28])=[CH:26][C:18]=1[F:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10878689N-tert-Butyl-3,5-dimethylbenzohydrazideHCID 214138374-Ethyl-2-fluorobenzoyl chloride

Product 1

HCID 99512763,5-Dimethyl-benzoic acid N-tert-butyl-N'-(4-ethyl-2-fluoro-benzoyl)-hydrazide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.150 g of 3,5-dimethyl-benzoic acid N-tert-butyl-hydrazide (1 eq, 0.68 mmol) and 0.110 mL (1.2 eq, 0.77 mmol) of 2-fluoro-4-ethyl benzoyl chloride were weighed into a 1 oz. vial. A small stirbar was added followed by 2 mL of methylene chloride. The mixture was stirred until the hydrazone dissolved. The stirring was stopped and 2 mL of a 1 M potassium carbonate (K2CO3) solution was added. The mixture was allowed to stir overnight. At the end of this period, 1 mL of water and 1 mL of methylene chloride were added. The aqueous phase was removed and the organic phase was washed twice with 1 M potassium carbonate solution. The organic phase was removed and dried over magnesium sulfate. The organic phase was filtered thru a pad of basic alumina and the solvent removed. The product, 3,5-dimethylbenzoic acid N-tert-butyl-N′-(2-fluoro-4-ethylbenzoyl)-hydrazide, was purified by trituration with 1:1 ether:hexane. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.7 (m, 2H), 7.6 (t, 1H), 7.0 (m, 3H), 2.6 (q, 2H), 2.3 (s, 3H), 2.1 (s, 6H), 1.5 (s, 9H), 1.1 (t, 3H).

Workup

  1. additionA small stirbar was added
  2. dissolutiondissolved
  3. customThe aqueous phase was removed
  4. washthe organic phase was washed twice with 1 M potassium carbonate solution
  5. customThe organic phase was removed
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe organic phase was filtered
  8. customthe solvent removed
  9. customThe product, 3,5-dimethylbenzoic acid N-tert-butyl-N′-(2-fluoro-4-ethylbenzoyl)-hydrazide, was purified by trituration with 1:1 ether

Sources & evidence

ORD record
ord-3191a557520540b499ae2421567b9514
Source dataset
uspto-grants-2013_09
Patent number
US08524948B2

Reaction notes

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