Propargyl bromide → HCID 59301824, compound

HRID 2236349Notes

Reaction equation

HRID 2236349 reaction equation
[CH3:1][C:2]([NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH3:17])[CH:10]=1)([CH3:6])[CH:3]([CH3:5])[CH3:4].[CH2:19](Br)[C:20]#[CH:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:6][C:2]([NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:21][C:20]#[CH:19])=[C:11]([O:16][CH3:17])[CH:10]=1)([CH3:1])[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 68582983HCID 68582983, compound

Product 1

HCID 59301824HCID 59301824, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10 ml of DMF were added 0.4 g of N-(1,1,2-trimethylpropyl)-4-hydroxy-3-methoxybenzamide, 0.28 g of propargyl bromide and 0.78 g of cesium carbonate and the mixture was heated under reflux for 1 hour. Then, the reaction mixture was concentrated. Dilute hydrochloric acid was added to the residue and extracted with ethyl acetate. After the organic layer was dried over magnesium sulfate, it was concentrated under reduced pressure. The solid obtained was successively washed with hexane and methyl tert-butyl ether to obtain 0.33 g of N-(1,1,2-trimethylpropyl)-4-(2-propynyloxy)-3-methoxybenzamide (hereinafter, described as the compound 11 of the present invention) represented by the formula:

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThen, the reaction mixture was concentrated
  4. additionDilute hydrochloric acid was added to the residue
  5. extractionextracted with ethyl acetate
  6. dry with materialAfter the organic layer was dried over magnesium sulfate, it
  7. concentrationwas concentrated under reduced pressure
  8. customThe solid obtained
  9. washwas successively washed with hexane and methyl tert-butyl ether

Sources & evidence

ORD record
ord-44cdf4836bea40fcbb57bcfad3bfe0ce
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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