Sodium Chloride → methyl N-[2-chloro-5-(3,3-dimethyl-1-butynyl)benzyl]carbamate

HRID 427245Notes

Reaction equation

HRID 427245 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[CH2:7][NH:8][C:9](=[O:12])[O:10][CH3:11].N1CCCCC1.[CH3:21][C:22]([CH3:26])([CH3:25])[C:23]#[CH:24].[Cl-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C1(C)C=CC=CC=1>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([C:24]#[C:23][C:22]([CH3:26])([CH3:25])[CH3:21])=[CH:13][C:6]=1[CH2:7][NH:8][C:9](=[O:12])[O:10][CH3:11]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 8082PiperidineHCID 135123,3-Dimethyl-1-butyneHCID 15483918methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamate

Product 1

HCID 15483917methyl N-[2-chloro-5-(3,3-dimethyl-1-butynyl)benzyl]carbamateYield 79.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

In a nitrogen atmosphere, 1.00 g of methyl N-(5-bromo-2-chlorobenzyl)carbamate, 0.20 g of tetrakis(triphenylphosphine)palladium, 0.07 g of copper(I) iodide and 10 ml of piperidine were added to 40 ml of toluene. To this mixed solution, 0.60 g of 3,3-dimethyl-1-butyne was added at 90° C., followed by stirring at 90° C. for 1 hour. The reaction solution was poured into a saturated sodium chloride aqueous solution and extracted with ethyl acetate, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.80 g of methyl N-[2-chloro-5-(3,3-dimethyl-1-butynyl)benzyl]carbamate as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b33d46370dec4938986ea45d0f400edd
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Reaction notes

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