Chloroacetyl chloride → 2-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide

HRID 1957980Notes

Reaction equation

HRID 1957980 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH2:8])(=[O:4])=[O:3].C(=O)([O-])O.[K+].[Cl:20][CH2:21][C:22](Cl)=[O:23].CC(C)=O.C(OC(C)C)(C)C>C(OCC)(=O)C.O>[Cl:20][CH2:21][C:22]([NH:8][C:7]1[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1)=[O:23]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 516893Potassium BicarbonateHCID 22221350Acetone diisopropyl etherHCID 673593153-(Methanesulfonyl)-5-nitroaniline

Product 1

HCID 684249082-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamideYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-(Methylsulfonyl)-5-nitro-aniline (4.3 g; 19.89 mmol) was diluted in 60 ml of ethyl acetate and a solution of potassium hydrogen carbonate (219 g, 21.87) in 10 ml of water was added. The reaction mixture was stirred at 0° C. and chloroacetylchloride (2.47 ml; 21.87 mmol) was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 2 h. Then, the phases were separated. The organic phase was dried on MgSO4 and concentrated under vacuum. The oil obtained was treated with acetone/di-isopropyl ether (1/5) and the solid obtained was filtered. 2.5 g (8.54 mmol; 43% yield) of the desired 2-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide were obtained.

Workup

  1. customto reach room temperature
  2. stirringstirred for 2 h
  3. customThen, the phases were separated
  4. customThe organic phase was dried on MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe oil obtained
  7. customthe solid obtained
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-7b7e2fb20a784deb9a298b513e4082d9
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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