Iodoethane → HCID 58020177, compound

HRID 1632115Notes

Reaction equation

HRID 1632115 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]2[CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)CC)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(I)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:32])[NH:7][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]2[CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 58019894HCID 58019894, compound

Product 1

HCID 58020177HCID 58020177, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthesis of [4-(3′-Chloro-6-methoxy-biphenyl-3-ylmethyl)-phenyl]-ethyl-carbamic acid tert-butyl ester (I-302) I-301 (140 mg, 0.33 mmol) was dissolved in 2 mL of DMF and stirred for 10 minutes under N2; then NaH was added. Once effervescence had ceased. ethyl iodide was added and the reaction mixture was stirred at room temperature for 2 hours and quenched with 20 mL of water. The mixture was extracted with ethyl acetate (3×5 mL), and the combined organic extracts were washed with brine and dried over Na2SO4. After filtration and removal of solvent, 120 mg (81%) of I-302 was collected.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 hours
  2. customquenched with 20 mL of water
  3. extractionThe mixture was extracted with ethyl acetate (3×5 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and removal of solvent, 120 mg (81%) of I-302
  7. customwas collected

Sources & evidence

ORD record
ord-356cd4bb14db4fe283ae4ce22cbdc032
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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