1-Iodopropane → HCID 14012385, compound

HRID 476957Notes

Reaction equation

HRID 476957 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:12]=[CH:13][CH:14]=1)[NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].[CH2:16]([Li])[CH2:17][CH2:18]C.ICCC>C1COCC1.CCCCCC.O>[CH2:15]([C:3]1[C:2]([Cl:1])=[CH:14][CH:13]=[CH:12][C:4]=1[NH:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 3

HCID 336431-IodopropaneHCID 4204423N-(3-chloro-2-methylphenyl)-2,2-dimethylpropanamideHCID 178418339Butyllithium3×

Product 1

HCID 14012385HCID 14012385, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 3-chloro-N-(2,2-dimethylpropionyl)-2-methylaniline (9.79 g) in dry THF (150 ml) was stirred under nitrogen at 0° while a solution of n-butyllithium in hexane was added in a dropwise fashion until a slight orange color was noted. The volume of n-butyllithium solution which had been added was noted, and an equal volume of this n-butyllithium solution was then added in order to complete formation of the dianion of the starting material. The final deep orange solution was then stirred at 0° for 15 min before adding iodopropane (7.92 g). After 15 min, the reaction mixture was cautiously diluted with water (250 ml) and was extracted with ethyl ether (300 ml). The organic layer was washed with brine, dried (MgSO4), and evaporated to afford the title compound as a white solid, 11.38 g (97% yield). Recrystallization from hexane provided an analytical sample, m.p. 88°-89°.

Workup

  1. additionwas added in a dropwise fashion until a slight orange color
  2. waitAfter 15 min
  3. extractionwas extracted with ethyl ether (300 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-728a6cbc474b4af9bf27a17d909bbd1d
Source dataset
uspto-grants-1989_12
Patent number
US04886800

Reaction notes

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