Dimethylamine → allyl 4-(N,N'-dimethylcarbamoyl)benzoate

HRID 840445Notes

Reaction equation

HRID 840445 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]([O:7][C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)=[O:9])[CH:5]=[CH2:6].O>C1COCC1>[CH3:1][N:2]([CH3:3])[C:14]([C:13]1[CH:17]=[CH:18][C:10]([C:8]([O:7][CH2:4][CH:5]=[CH2:6])=[O:9])=[CH:11][CH:12]=1)=[O:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 226194734-(Allyloxycarbonyl)benzoyl chloride

Product 1

HCID 22619405allyl 4-(N,N'-dimethylcarbamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 ml of dimethylamine (40% in water) were introduced into a round-bottomed flask and a solution of 2.5 g (11.6 mmol) of 4-(allyloxycarbonyl)benzoyl chloride in 50 ml of THF was added dropwise. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. 2.7 g (100%) of the expected amide were recovered in the form of a slightly yellow oil.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. custom2.7 g (100%) of the expected amide were recovered in the form of a slightly yellow oil

Sources & evidence

ORD record
ord-de37339664054bf3810e12f1ab0abc8b
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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