Hexane → HCID 13206063, compound

HRID 1583937Notes

Reaction equation

HRID 1583937 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[Cl:15].C(N(CC)CC)C.Cl[C:24]([CH3:28])([CH3:27])[C:25]#[CH:26].CCCCCC>O1CCOCC1.O.[Cu]Cl>[Cl:15][C:3]1[CH:4]=[C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:24]([CH3:28])([CH3:27])[C:25]#[CH:26]

Participants

8

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 706791-Butyne, 3-chloro-3-methyl-HCID 12854202HCID 12854202, compound

Product 1

HCID 13206063HCID 13206063, compoundYield 50.8%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

9.3 g of Ethyl 2-(4-amino-3-chlorophenyl)propionate were dissolved in a mixture of 100 ml of dioxane and 30 ml of water. 1.0 g of copper(I) chloride and 10 ml of triethylamine were further added to the solution. 6.3 g of 3-chloro-3-methyl-1-butyn was added dropwise thereto with stirring under nitrogen atmosphere. The mixture was reacted at 5° C. for 2 hours, followed by addition of a mixture of hexane and water and then separation of the organic layer. The organic layer was washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then the solvent was distilled off. The residue was purified by column chromatography on silica gel (eluted with benzene) to give 6.1 g of ethyl 2-[3-chloro-4-(1,1-dimethyl-2-propynylamino)phenyl]propionate (Compound 1).

Workup

  1. customThe mixture was reacted at 5° C. for 2 hours
  2. customseparation of the organic layer
  3. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography on silica gel (eluted with benzene)

Sources & evidence

ORD record
ord-d5f531341694473d9f9a858814d784ef
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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