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

HRID 1639464Notes

Reaction equation

HRID 1639464 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-c709124ceb7d4f4d939fd277476415aa
Source dataset
uspto-grants-1989_11
Patent number
US04883914

Reaction notes

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