Sodium hydride → HCID 58829446, compound

HRID 2200150Notes

Reaction equation

HRID 2200150 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([NH:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18]Cl)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1>C1COCC1>[NH2:3][C:4]1[CH:5]=[C:6]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:20])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 90020591HCID 90020591, compound

Product 1

HCID 58829446HCID 58829446, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add sodium hydride (60%, 65 mg, 1.64 mmol) portionwise to the solution of N-(3-amino-5-(trifluoromethyl)phenyl)-4-chlorobutanamide (230 mg, 0.82 mmol) in THF (5 mL), stir the resulting mixture for 2 hrs at ambient temperature. Quench the reaction with water, extract the mixture with ethyl acetate, wash the organic layer with water and brine sequentially, and dry over anhydrous sodium sulfate, concentrate to give brownish oil. Purify by flash chromatography (silica gel, PE:EtOAc=1:1) to yield white solid as the title compound (180 mg, 90%). MS: (M+1): 245.1.

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract the mixture with ethyl acetate
  4. washwash the organic layer with water and brine sequentially
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationconcentrate
  7. customto give brownish oil
  8. customPurify by flash chromatography (silica gel, PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-09364e0c026d4287bbae924e2eb246f1
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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