Hydrogen Peroxide → Methyl 4-carbamoyl-2-chlorobenzoate

HRID 1978201Notes

Reaction equation

HRID 1978201 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[Cl:12].C(=O)([O-])[O-:15].[K+].[K+].OO>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH2:11])=[O:15])=[CH:6][C:5]=1[Cl:12]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 53845357Methyl 2-chloro-4-cyanobenzoate

Product 1

HCID 53785786Methyl 4-carbamoyl-2-chlorobenzoateYield 498%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-chloro-4-cyano benzoic acid methyl ester (12.4 g, 63.4 mmol) and potassium carbonate (1.3 g, 9.4 mmol) in dimethylsulfoxide (40 mL) was treated dropwise under cooling with 30% hydrogen peroxide (7.6 mL). The mixture was allowed to warm to room temperature and stirred overnight. The solution was quenched with water and the resulting precipitate collected by filtration. The crude material was dissolved in dichloromethane and absorbed on a silica gel Merck-60 flash column. Elution with a dichloromethane-methanol gradient (from 98:2 to 90:10) provided the title compound (10 g) as a white solid, m.p. 154-156° C.

Workup

  1. additionwas treated dropwise
  2. customThe solution was quenched with water
  3. filtrationthe resulting precipitate collected by filtration
  4. dissolutionThe crude material was dissolved in dichloromethane
  5. customabsorbed on a silica gel Merck-60 flash column
  6. washElution with a dichloromethane-methanol gradient (from 98:2 to 90:10)

Sources & evidence

ORD record
ord-0df37480ccc4460abd23ad8bb871975f
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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