Hydrochloric Acid → N-(3-acetyl-5-cyanophenyl)methanesulfonamide

HRID 251828Notes

Reaction equation

HRID 251828 reaction equation
[Al](C)(C)C.[CH3:5]NCCNC.CO[C:13](=[O:27])[C:14]1[CH:19]=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[C:16]([C:25]#[N:26])[CH:15]=1.Cl>C1(C)C=CC=CC=1>[C:13]([C:14]1[CH:19]=[C:18]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH:17]=[C:16]([C:25]#[N:26])[CH:15]=1)(=[O:27])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8070N,N'-DimethylethylenediamineHCID 16682925TrimethylaluminumHCID 57686818Methyl-3-cyano-5-(methylsulfonamido)benzoate

Product 1

HCID 57686801N-(3-acetyl-5-cyanophenyl)methanesulfonamideYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Al(CH3)3 (20 mmol) was added dropwise to the ice-water cooled solution of DMEDA (4.4 mmol) in dry toluene (60 mL) under nitrogen. After addition, it was continued to stir for 2 hours at room temperature. Then, methyl-3-cyano-5-(methylsulfonamido)benzoate (4 mmol) was added, and the reaction mixture was heated to reflux overnight. After cooling, it was poured into diluted hydrochloric acid, the mixture was extracted with EtOAc, the combined organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated to afford N-(3-acetyl-5-cyanophenyl)methanesulfonamide with a yield of 35%. Br2 (1.2 mmol) was added dropwise to the solution of N-(3-acetyl-5-cyanophenyl)methanesulfonamide (1 mmol) in Et2O (50 mL). After addition, it was continued to stir for 1.5 hours. Then the reaction mixture was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated to afford N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide with a yield of 85%.

Workup

  1. additionAfter addition, it
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux overnight
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with EtOAc
  6. washthe combined organic layer was washed with water and brine sequentially
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ec9d98c3c3ce4b13aba24c0aa2b65108
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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