Potassium Carbonate → Hydrazinecarboxylic acid, 2-(2-ethyl-3-methoxybenzoyl)-, 1,1-dimethylethyl ester

HRID 403166Notes

Reaction equation

HRID 403166 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16]([C:18]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])[CH3:17]>C(Cl)Cl.O>[C:1]([O:5][C:6]([NH:7][NH:8][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:18]=1[CH2:16][CH3:17])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70091tert-Butyl carbazateHCID 221445622-Ethyl-3-methoxybenzoyl chloride

Product 1

HCID 59016613Hydrazinecarboxylic acid, 2-(2-ethyl-3-methoxybenzoyl)-, 1,1-dimethylethyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Tert-butylcarbazate (80.0 g, 605 mmol) was stirred in 800 mL methylene chloride and cooled to 0° C. To this was added the potassium carbonate solution (937 g, 847 mmol). 2-Ethyl-3-methoxybenzoyl chloride (132 g, 666 mmol) was dissolved in 400 mL of methylene chloride and added to the reaction mixture dropwise over 15 minutes. The mixture was stirred at 0° C. for 15 min, then at room temperature for 18 hours. The reaction was diluted with more methylene chloride and water. The aqueous phase was separated. The remaining organic phase was washed with 1N HCl, water, saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue was triturated with hexane to give a white solid, N′-(2-ethyl-3-methoxy-benzoyl)-hydrazinecarboxylic acid tert-butyl ester (167 g, 567 mmol) in 94% yield. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.4 (br s, 1H), 7.22 (t, 1H), 7.03 (br d, 1H), 6.95 (d, 1H), 6.65 (br, 1H), 3.84 (s, 3H), 2.8 (q, 2H), 1.51 (s, 9H), 1.2 (t, 3H).

Workup

  1. additionadded to the reaction mixture dropwise over 15 minutes
  2. waitat room temperature for 18 hours
  3. customThe aqueous phase was separated
  4. washThe remaining organic phase was washed with 1N HCl, water, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-85987f5eebb94419b10612b7095f99e1
Source dataset
uspto-grants-2014_06
Patent number
US08748125B2

Reaction notes

Loading…