Allyl bromide → HCID 68539410, compound

HRID 1432120Notes

Reaction equation

HRID 1432120 reaction equation
[CH:1]1([NH:4][C:5](=[O:15])[C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20]>C1COCC1>[CH2:20]([N:4]([CH:1]1[CH2:3][CH2:2]1)[C:5](=[O:15])[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 43452679852879-04-0

Product 1

HCID 68539410HCID 68539410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 0.3 g (1.37 mmol) N-cyclopropyl-isophthalamic acid in 10 ml THF is treated with 142 mg (3.55 mmol) NaH (60% suspension in mineral oil) and stirred at 25° C. After 2 h 0.27 ml (3.23 mmol) allylbromide is added and after 18 h the reaction is quenched with water. The mixture is acidified with 2N HCl and extracted with EtOAc. The organic phase is washed with brine, dried with sodium sulfate and evaporated to yield the title compound that is used in the next step without purification.

Workup

  1. customis quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e058e4cb927646d8806e4a29127fa832
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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