Potassium Carbonate → 3,5-dimethoxy-4-methyl-benzoic acid N-(1-ethyl-2,2-dimethyl-propyl)-N'-(3-methoxy-2-methyl-benzoyl)-hydrazide

HRID 39646Notes

Reaction equation

HRID 39646 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([CH:13]([NH:18][NH:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:22]=1[CH3:29])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:12].[C:31]([O-:34])([O-])=O.[K+].[K+].[C:37]([O-])(O)=[O:38].[Na+]>C(Cl)Cl>[CH2:11]([CH:13]([N:18]([C:6](=[O:7])[C:5]1[CH:9]=[C:10]([O:38][CH3:37])[C:2]([CH3:1])=[C:3]([O:34][CH3:31])[CH:4]=1)[NH:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:22]=1[CH3:29])[C:14]([CH3:17])([CH3:15])[CH3:16])[CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 134054-Methylbenzoyl ChlorideHCID 516892Sodium BicarbonateHCID 598386283-methoxy-2-methyl-benzoic acid N'-(1-ethyl-2,2-dimethyl-propyl)-hydrazide

Product 1

HCID 598385963,5-dimethoxy-4-methyl-benzoic acid N-(1-ethyl-2,2-dimethyl-propyl)-N'-(3-methoxy-2-methyl-benzoyl)-hydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 20 mL vial was added 161 mg (0.75 mmol) of 3,5 dimethoxy, 4-methyl benzoyl chloride, a 5 mL solution of 3-methoxy-2-methyl-benzoic acid N′-(1-ethyl-2,2-dimethyl-propyl)-hydrazide, and 1.5 mL of aqueous 25% K2CO3. The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was transferred to a separatory funnel with CH2Cl2 and shaken with dilute aqueous NaHCO3. The organic phase was dried, concentrated and chromatographed on silica. 100 mg of pure product, 3,5-dimethoxy-4-methyl-benzoic acid N-(1-ethyl-2,2-dimethyl-propyl)-N′-(3-methoxy-2-methyl-benzoyl)-hydrazide, was eluted with 25% ethyl acetate/hexane. TLC: Rf=0.54 (1:1 ethyl acetate:hexane); 1H NMR (CDCl3, 300 MHz) δ (ppm): 6.6-7.2 (m, 4H), 6.25 (d, 1H), 4.6 (d, 1H), 3.8-3.95 (br s, 9H), 2.1 (br s, 3H), 1.9 (s, 3H), 1.6 (br, 2H), 1.3 (m, 3H), 0.9-1.2 (br d, 9H).

Workup

  1. customThe organic phase was dried
  2. concentrationconcentrated
  3. customchromatographed on silica
  4. wash100 mg of pure product, 3,5-dimethoxy-4-methyl-benzoic acid N-(1-ethyl-2,2-dimethyl-propyl)-N′-(3-methoxy-2-methyl-benzoyl)-hydrazide, was eluted with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-19ee800ac70e450d975659f674e1a8c6
Source dataset
uspto-grants-2013_09
Patent number
US08524948B2

Reaction notes

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