Triethylamine → 2,3-dimethyl-2-propionamido-N-(p-tolylsulfonyl)butyramide

HRID 1655842Notes

Reaction equation

HRID 1655842 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].C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>C1(C)C=CC=CC=1>[CH3:20][C:3]([NH:2][C:28](=[O:31])[CH2:29][CH3:30])([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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 200898702-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride

Product 1

HCID 146957612,3-dimethyl-2-propionamido-N-(p-tolylsulfonyl)butyramide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride (1.2 g, 5.3 mol) is dissolved in 25 mL of toluene under N2. Then triethylamine (1.9 mL, 2.5 equivalents) is added, followed by immediate addition of propionyl chloride (0.55 mL, 6.36 mol). The reaction mixture is heated for one hour, and then solvents are removed under reduced pressure. The yellowish residue is recrystallized from EtOH/water, to yield the title product as a white solid having mp 166°-168° C.

Workup

  1. temperatureThe reaction mixture is heated for one hour
  2. customsolvents are removed under reduced pressure
  3. customThe yellowish residue is recrystallized from EtOH/water

Sources & evidence

ORD record
ord-4f9f4f68c7354a9ea9eaf0da8b4e2c86
Source dataset
uspto-grants-1993_10
Patent number
US05252539

Reaction notes

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