Dimethylformamide → tert.-Butyl (3-chloropropyl)-[2-(4-cyanophenyl)ethyl]carbamate

HRID 1591757Notes

Reaction equation

HRID 1591757 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:7][CH:6]=1)#[N:4].CN(C)C=O.Br[CH2:27][CH2:28][CH2:29][Cl:30]>O1CCCC1>[Cl:30][CH2:29][CH2:28][CH2:27][N:13]([CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=1)[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 21955533tert-Butyl 4-cyanophenethylcarbamate

Product 1

HCID 58638721tert.-Butyl (3-chloropropyl)-[2-(4-cyanophenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 0.23 g (9.03 mmol) of sodium hydride (95%) was added to a solution of 1.482 g (6.02 mmol) of tert.-butyl [2-(4-cyanophenyl)ethyl]carbamate in 25 ml of tetrahydrofuran/25 ml of dimethylformamide. The mixture was stirred for a further 15 minutes. 1.49 ml (15.04 mmol) of 1-bromo-3-chloropropane were then added, and the reaction mixture was stirred at room temperature overnight. With ice bath cooling, the mixture was then quenched with water, and extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 4:1).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. temperatureWith ice bath cooling
  3. customthe mixture was then quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-adc6e36eafb94085ac6bf8a246d1351a
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

Loading…