Dimethylformamide → 2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide

HRID 1639466Notes

Reaction equation

HRID 1639466 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:11])[C:5]([CH3:10])([CH:7]([CH3:9])[CH3:8])[N:6]=1.CN(C=O)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.[Na]>C1COCC1>[C:2]([NH:6][C:5]([CH3:10])([CH:7]([CH3:9])[CH3:8])[C:4]([NH:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:24])=[O:25])=[O:11])(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 146957652,4-Dimethyl-4-isopropyl-2-oxazolin-5-oneHCID 66664522Sodium p-toluene sulfonamide

Product 1

HCID 146246882-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dimethyl-4-isopropyl-2-oxazolin-5-one (2.0 g) is mixed with DMF (50 mL), THF (70 mL) and sodium p-toluene sulfonamide (5.0 g), and the resulting mixture is heated at reflux for 16 hours. At the end of this time the mixture is cooled, and the solvents are removed under vacuum. The residue is mixed with water and the pH adjusted to 8 with NaHCO3. The aqueous mixture is extracted with ethyl acetate and the organic layers are discarded. The aqueous mixture is acidified to pH≈4 with HCl and saturated with NaCl and extracted with ethyl acetate. The organic extracts are combined, dried over MgSO4, filtered and evaporated to give 0.66 of the title product.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 16 hours
  3. temperatureAt the end of this time the mixture is cooled
  4. customthe solvents are removed under vacuum
  5. additionThe residue is mixed with water
  6. extractionThe aqueous mixture is extracted with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8088999de7e14282bb0914eb6c4306ef
Source dataset
uspto-grants-1989_11
Patent number
US04883914

Reaction notes

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