Allyl bromide → 3-(N-methyl-allyloxycarbamoyl)-5-nitro-benzoic acid allyl ester

HRID 1263606Notes

Reaction equation

HRID 1263606 reaction equation
[CH2:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([C:15](=[O:19])[N:16]([OH:18])[CH3:17])[CH:7]=1)[CH:2]=[CH2:3].[CH2:21](Br)[CH:22]=[CH2:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([C:15](=[O:19])[N:16]([O:18][CH2:23][CH:22]=[CH2:21])[CH3:17])[CH:7]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 229861013-(N-methyl-hydroxycarbamoyl)-5-nitro-benzoic acid allyl ester

Product 1

HCID 229861003-(N-methyl-allyloxycarbamoyl)-5-nitro-benzoic acid allyl esterYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (8(a)) (0.60 g), allyl bromide (0.28 g), potassium carbonate (0.59 g) and DMF (20 ml) was stirred for 3 hours at ambient temperature under an argon atmosphere. The dimethyl formamide was then evaporated under reduced pressure and the residue dissolved in ethyl acetate (50 ml) and water (50ml). The organic phase was separated, washed with brine (50 ml), dried over magnesium sulphate and evaporated under reduced pressure to dryness to give 3-(N-methyl-allyloxycarbamoyl)-5-nitro-benzoic acid allyl ester (8(b)) as a yellow oil (0.571 g).

Workup

  1. customThe dimethyl formamide was then evaporated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (50 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-c23a47d36c474d0996dc1485abe2d332
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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