Potassium Carbonate → HCID 10412259, compound

HRID 919002Notes

Reaction equation

HRID 919002 reaction equation
[C:1]([CH:5]([NH:12][NH:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1[CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[C:29](Cl)=[O:30].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:1]([CH:5]([N:12]([C:29](=[O:30])[C:28]1[CH:32]=[C:33]([CH3:35])[CH:34]=[C:26]([CH3:25])[CH:27]=1)[NH:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1[CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 59016575HCID 59016575, compound

Product 1

HCID 10412259HCID 10412259, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

164 mg (0.49 mmol) of 3-methoxy-2-methyl-benzoic acid N′-(1-tert-butyl-heptyl)-hydrazide and 82 mg 3,5-dimethylbenzoyl chloride were dissolved in 10 mL CH2Cl2. 7 mL of 25% K2CO3 were added, and the reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC. The phases were separated, adding additional CH2Cl2 and/or water as needed to aid manipulation. The CH2Cl2 layer was dried and solvent was removed in vacuo to provide 240 mg of crude product. This material was purified by silica gel column chromatography, eluting with a step gradient of 5-20% ethyl acetate in hexane. The desired product eluted in the 15% ethyl acetate fraction, TLC Rf=0.62 (1:1 ethyl acetate:hexane), to yield 195 mg 3,5-dimethyl-benzoic acid N-(1-tert-butyl-heptyl)-N′-(3-methoxy-2-methyl-benzoyl)-hydrazide. 1H NMR (500 MHz, CDCl3) δ (ppm): 7.2 (s, NH), 7.05 (s, 2H), 7.03 (m, 1H), 7.01 (s, 1H), 6.83 (d, 1H), 6.25 (d, 1H), 4.67 (d, 1H), 3.81 (s, 3H), 2.28 (s, 6H), 1.79 (s, 3H), 1.55 (br m, 2H), 1.3 (br, 8H), 1.34+1.07 (s+s, 9H), 0.089 (br s, 3H).

Workup

  1. customThe phases were separated
  2. additionadding additional CH2Cl2 and/or water
  3. dry with materialThe CH2Cl2 layer was dried
  4. customsolvent was removed in vacuo
  5. customto provide 240 mg of crude product
  6. customThis material was purified by silica gel column chromatography
  7. washeluting with a step gradient of 5-20% ethyl acetate in hexane
  8. washThe desired product eluted in the 15% ethyl acetate fraction, TLC Rf=0.62 (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-f2f062a391f04daebba064a91ff2d656
Source dataset
uspto-grants-2016_03
Patent number
US09272986B2

Reaction notes

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