Benzoyl chloride → HCID 68513157, compound

HRID 2243203Notes

Reaction equation

HRID 2243203 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][NH:5][C:4](=[O:7])[CH:3]1[O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=1.[H-].[Na+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH4+].[Cl-]>C1COCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[C:24]([N:5]1[CH2:6][C:2]([CH3:21])([CH3:1])[CH:3]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:18])([F:20])[F:19])[CH:10]=2)[C:4]1=[O:7])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 56670277HCID 56670277, compound

Product 1

HCID 68513157HCID 68513157, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 4-(4,4-dimethyl-2-oxo-pyrrolidin-3-yloxy)-2-trifluoromethyl-benzonitrile (Product of Example 3, 250 mg, 0.84 mmol) in anhydrous THF (5 mL) was added NaH (40 mg, 1 mmol) under N2 at RT (room temperature). After stirring for 15 minutes, benzoyl chloride was added (0.14 mL, 1 mmol) as a solution in THF (1 mL). After stirring at RT overnight sat. NH4Cl (25 mL) and ethyl acetate (150 mL) were added. The separated organic phase was treated with brine and dried over MgSO4. The solution was then filtered, concentrated down, and purified by column chromatography (small Biotage silica gel column, 2:1 Hex/EA). Combined cleanest fractions to afford the desired product as a white solid.

Workup

  1. additionwere added
  2. dry with materialdried over MgSO4
  3. filtrationThe solution was then filtered
  4. concentrationconcentrated down
  5. custompurified by column chromatography (small Biotage silica gel column, 2:1 Hex/EA)

Sources & evidence

ORD record
ord-095c7a2dc5ad432b828089562f07e5e5
Source dataset
uspto-grants-2010_03
Patent number
US07674819B2

Reaction notes

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