Sodium hydride → HCID 67355682, compound

HRID 1670834Notes

Reaction equation

HRID 1670834 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH2:5][CH2:4]1.[H-].[Na+].[Br:17][C:18]1[CH:19]=[C:20]([Cl:27])[C:21]([CH2:25]Br)=[C:22]([Cl:24])[CH:23]=1>CN(C=O)C>[Br:17][C:18]1[CH:19]=[C:20]([Cl:27])[C:21]([CH2:25][N:11]2[CH2:12][CH2:13][CH:9]([CH:6]3[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:8][CH2:7]3)[C:10]2=[O:14])=[C:22]([Cl:24])[CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 594744985-Bromo-2-(bromomethyl)-1,3-dichlorobenzeneHCID 67356492HCID 67356492, compound

Product 1

HCID 67355682HCID 67355682, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 3-(4-methoxycyclohexyl)-pyrrolidin-2-one (0.0.71 g, 3.6 mmol) in DMF (20 mL) with a sodium hydride (0.0.29 mL, 7.2 mmol) and stir at room temperature for 10 minutes under N2. Treat the reaction with 5-Bromo-2-bromomethyl-1,3-dichloro-benzene (1.36 g, 4.3 mmol). Stir the mixture for 14 hours. Quench the reaction with water and extract with ethyl acetate. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with 25% ethyl acetate in hexanes to afford 0.45 g of the title compound.

Workup

  1. additionTreat
  2. stirringStir the mixture for 14 hours
  3. customQuench
  4. customthe reaction with water
  5. extractionextract with ethyl acetate
  6. dry with materialDry the organic layer (Na2SO4)
  7. customremove the solvent in vacuo
  8. customto afford crude product
  9. custompurify with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2ed59242f4b440ea8763bdc997ee4e2d
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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