Hydrochloric Acid → HCID 86628293, compound

HRID 21251Notes

Reaction equation

HRID 21251 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][CH2:13][O:14][CH3:15])=[O:2].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:38]([NH2:47])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([CH3:40])[CH3:39].Cl>CN(C=O)C.O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:47][C:38]([CH3:40])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH3:39])=[O:9])=[CH:5][C:4]=1[O:12][CH2:13][O:14][CH3:15])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 866282924-Formyl-3-methoxymethoxybenzoic acid

Product 1

HCID 86628293HCID 86628293, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4-Formyl-3-methoxymethoxybenzoic acid (2.57 g, 12.2 mmol) was dissolved in DMF (50 mL), and the solution was added with EDCI (4.68 g, 24.4 mmol), HOBT monohydrate (1.65 g, 12.2 mmol) and cumylamine (4.03 mL, 24.4 mmol), followed by stirring at room temperature for 4 hours. The reaction mixture was added with water (10 mL) and 1 mol/L hydrochloric acid (10 mL) and stirred at room temperature for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30) to obtain 4-formyl-3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (3.12 g, yield 78%).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialby drying over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30)

Sources & evidence

ORD record
ord-3bbf80376b0f4c05ab93e397b1118499
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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