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

HRID 275046Notes

Reaction equation

HRID 275046 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-b80e6d3cffdb4c86ba1611f97d6de656
Source dataset
uspto-grants-1995_02
Patent number
US05391757

Reaction notes

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