Propargyl bromide → HCID 15669662, compound

HRID 1965962Notes

Reaction equation

HRID 1965962 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[OH-].[K+].[CH2:10](Br)[C:11]#[CH:12]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[CH2:12]([N:4]1[C:5](=[O:6])[CH2:7][NH:1][C:2]1=[O:3])[C:11]#[CH:10]

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 10006HydantoinHCID 14797Potassium Hydroxide

Product 1

HCID 15669662HCID 15669662, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of hydantoin (10 g, 100 mmol) in THF (150 mL) add tetrabutylammonium bromide (4 g, 12.3 mmol), potassium hydroxide (5.6 g, 100 mmol) and then propargyl bromide (11.9 g, 100 mmol). Heat the mixture to 75° C. for 18 h. Dilute the mixture with EtOAc (200 mL), wash with water (2×100 mL) and 1N aqueous HCl (100 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo to obtain the title compound as a yellow powder (8.3 g, 60%). Triturate the solid with diethyl ether (100 mL) to obtain the title compound as a white crystalline solid (7.8 g, 56%).

Workup

  1. washwash with water (2×100 mL) and 1N aqueous HCl (100 mL)
  2. dry with materialDry the organic phase over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-c76458333c7b4e76a0fe5ef96155123f
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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