Dimethylformamide → 4-(3,3-Diethoxypropoxy)benzamide

HRID 1183798Notes

Reaction equation

HRID 1183798 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.Cl[CH2:23][CH2:24][CH:25]([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>O>[CH2:27]([O:26][CH:25]([O:29][CH2:30][CH3:31])[CH2:24][CH2:23][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1)[CH3:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 962173-Chloro-1,1-diethoxypropane

Product 1

HCID 636301464-(3,3-Diethoxypropoxy)benzamideYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

500 mg of 4-hydroxybenzamide, 1.51 g of potassium carbonate, 10 mL of DMF and 730 mg of 3-chloro-1,1-diethoxypropane are added to a flask. The reaction mixture is stirred at 100° C. for 18 hours and then 5 mL of water are added. The aqueous phase is extracted with ethyl acetate, and then the organic phases are collected, washed with water and concentrated under reduced pressure. The product is obtained in the form of a powder in a yield of 89% and with a chemical purity of 95%.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. customthe organic phases are collected
  3. washwashed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe product is obtained in the form of a powder in a yield of 89% and with a chemical purity of 95%

Sources & evidence

ORD record
ord-418e558c77e84a3a9d574cec4a768442
Source dataset
uspto-grants-2014_03
Patent number
US08664408B2

Reaction notes

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