Triethylamine → N-(2,4,6-triisopropylbenzylsulfonyl)-2-(2,6-diisopropylphenyl)acetamide

HRID 2396263Notes

Reaction equation

HRID 2396263 reaction equation
[CH:1]([C:4]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[C:11]([CH:18]([CH3:20])[CH3:19])[C:5]=1[CH2:6][S:7]([NH2:10])(=[O:9])=[O:8])([CH3:3])[CH3:2].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[CH2:33][C:34](Cl)=[O:35])([CH3:23])[CH3:22].CCN(CC)CC>C1COCC1>[CH3:32][CH:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH:21]([CH3:22])[CH3:23])[C:25]=1[CH2:33][C:34]([NH:10][S:7]([CH2:6][C:5]1[C:11]([CH:18]([CH3:20])[CH3:19])=[CH:12][C:13]([CH:15]([CH3:17])[CH3:16])=[CH:14][C:4]=1[CH:1]([CH3:3])[CH3:2])(=[O:9])=[O:8])=[O:35])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 190465392,4,6-TriisopropylbenzylsulfonamideHCID 193627822,6-Diisopropylphenylacetyl chloride

Product 1

HCID 9828098N-(2,4,6-triisopropylbenzylsulfonyl)-2-(2,6-diisopropylphenyl)acetamideYield 12.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4,6-triisopropylbenzylsulfonamide (100 mg, 0.33 mmol), 2,6-diisopropylphenylacetyl chloride (75 mg, 0.34 mmol), and Et3N (47 μL, 0.34 mmol) in 10 mL THF was stirred at room temperature overnight. The solvent was evaporated and the residue was distributed between ethyl acetate and 0.1N HCl, the organic layer was washed with brine, dried, and evaporated. The pure product (20 mg, 12%) was isolated by column chromatography (4:1 hexane:EtOAc), m/e=499; NMR (CDCl3): δ 7.05-7.4 (m, 5H), 4.25 (s, 2H), 3.95 (s, 2H), 3.45-3.6 (m, 1H), 3.0-3.15 (m, 2H), 2.85-3.0 (m, 2H), 1.05-1.4 (m, 30H) ppm.

Workup

  1. customThe solvent was evaporated
  2. washthe organic layer was washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-939e5efd586a4a8e9223a309e9555aaf
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

Loading…