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

HRID 981433Notes

Reaction equation

HRID 981433 reaction equation
Cl.[NH2:2][C:3]([CH3:20])([CH:17]([CH3:19])[CH3:18])[C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5].C1C[O:24][CH2:23][CH2:22]1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:23]([NH:2][C:3]([CH3:20])([CH:17]([CH3:18])[CH3:19])[C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5])(=[O:24])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 200898702-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino2,3-dimethyl-N-(p-tolylsulfonyl) butyramide hydrochloride (45 g~0.4 mols) is completely dissolved in 160 mL of pyridine and 500 mL of THF is added. Acetic anhydride (45 mL) is then poured into the solution and the reaction mixture is heated at reflux for one hour. The solvents are removed under reduced pressure, and the oily residue is crystallized from EtOH/water affording 33.09 g of the title product having m.p. 198°-199° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for one hour
  3. customThe solvents are removed under reduced pressure
  4. customthe oily residue is crystallized from EtOH/water affording 33.09 g of the title product

Sources & evidence

ORD record
ord-6a961d7893e8452bb3f6269368f2f905
Source dataset
uspto-grants-1991_02
Patent number
US04992094

Reaction notes

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