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

HRID 1742512Notes

Reaction equation

HRID 1742512 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-2ee90ff454e04e6b811a21eb01d2b3a2
Source dataset
uspto-grants-1994_08
Patent number
US05338883

Reaction notes

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