Sulfur → sec-Butyl 5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate

HRID 1650884

Reaction equation

HRID 1650884 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([CH3:16])=[C:7]([CH:15]=1)[C:8]([O:10][CH:11]([CH2:13][CH3:14])[CH3:12])=[O:9])[CH3:2].[CH3:17][C@@:18]([C:23]([NH2:25])=[O:24])([CH:20]([CH3:22])[CH3:21])[NH2:19].[S]>ClC1C=CC=CC=1.C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:16]2[NH:25][C:23](=[O:24])[C:18]([CH:20]([CH3:22])[CH3:21])([CH3:17])[N:19]=2)=[C:7]([CH:15]=1)[C:8]([O:10][CH:11]([CH2:13][CH3:14])[CH3:12])=[O:9])[CH3:2]

Participants

6

Reactant 3

HCID 5362487SulfurHCID 10154071(S)-2-Amino-2,3-dimethylbutanamideHCID 15077472Sec-butyl 5-ethyl-2-methylnicotinate

Product 1

HCID 23053208sec-Butyl 5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinateYield 72.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2.2 g of sec-butyl 5-ethyl-2-methylnicotinate (10 mmol), 1.3 g of a-methylvalinamide (10 mmol) and 2.0 g of sulfur (62 mmol) in 2.5 g of chlorobenzene (114 wt%) is magnetically stirred at reflux temperatures for 24 hours. The reaction is cooled, diluted with methylene chloride, and filtered to remove unreacted sulfur. The filtrate is chromatographed on silica gel using 2:1 hexane-ethyl acetate as eluant to afford 2.5 g of the title product (72% yield) as a solid; recrystallization from ether-hexane gives mp 83°-87° C.

Workup

  1. temperatureat reflux temperatures for 24 hours
  2. temperatureThe reaction is cooled
  3. filtrationfiltered
  4. customto remove unreacted sulfur
  5. customThe filtrate is chromatographed on silica gel using 2:1 hexane-ethyl acetate as eluant

Sources & evidence

ORD record
ord-708a4f7f892941ab8d630804b72473f8
Source dataset
uspto-grants-1990_05
Patent number
US04925944

Linked notes

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