Sodium hydride → HCID 11523028, compound

HRID 2235258Notes

Reaction equation

HRID 2235258 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].[H-].[Na+].Br[CH:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:14]1=[O:24]>O1CCCC1>[CH:18]1([N:15]2[CH2:16][CH2:17][CH:13]([S:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[C:14]2=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707302,4-DichlorobenzenethiolHCID 121898363-Bromo-1-cyclohexylpyrrolidin-2-one

Product 1

HCID 11523028HCID 11523028, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Place 2,4-dichloro-benzenethiol (728 mg, 4.1 mmol) in tetrahydrofuran (10 mL) and cool to 0° C. Slowly add sodium hydride (98 mg, 4.1 mmol) and stir for 30 minutes. To this solution, add a solution of 3-bromo-1-cyclohexyl-pyrrolidin-2-one (Preparation 1) in tetrahydrofuran (2 mL) and stir at room temperature for 30 minutes. Pour reaction mixture onto ice and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-30% ethyl acetate in hexane) to yield 641 mg (92%) of the title compound: Mass spectrum (apci) m/z=344.1 (M+H).

Workup

  1. additionPour
  2. customreaction mixture onto ice
  3. extractionextract with methylene chloride
  4. dry with materialDry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel (20-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a9db57edf6b5403a9c03a2c294e6b7f9
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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