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

HRID 892939Notes

Reaction equation

HRID 892939 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-Amino-2,3-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-0966faeffd844c3da0d7f0c1440b3fe5
Source dataset
uspto-grants-1992_06
Patent number
US05120854

Reaction notes

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