Hydrochloric Acid → HCID 84716661, compound

HRID 2200155Notes

Reaction equation

HRID 2200155 reaction equation
[F:1][C:2]([C:5]1[CH:6]=[C:7]([N:11]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]=[N:9][CH:10]=1)([F:4])[CH3:3].O.Cl.C1COCC1>CCOC(C)=O>[F:1][C:2]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[N:9][CH:10]=1)([F:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 90020358HCID 90020358, compound

Product 1

HCID 84716661HCID 84716661, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add 5-(1,1-difluoroethyl)-N-(diphenylmethylene)pyridin-3-amine (296 mg, 0.92 mmol), water (1 mL) and hydrochloric acid (1N, 4 mL) to THF (10 mL), stir at room temperature for 3 hrs. TLC (PE:EtOAc=2:1) shows the reaction is complete. Extract the mixture with ethyl acetate, wash the organic layer with saturated sodium bicarbonate solution and brine sequentially, and dry over anhydrous sodium sulfate. Concentrate under reduced pressure to give the crude product. Purification by flash chromatography (silica gel, EtOAc:PE=1:1) yields the title compound (140 mg, 96.5%). MS: (M+1): 159.2.

Workup

  1. extractionExtract the mixture with ethyl acetate
  2. washwash the organic layer with saturated sodium bicarbonate solution and brine sequentially
  3. dry with materialdry over anhydrous sodium sulfate
  4. concentrationConcentrate under reduced pressure
  5. customto give the crude product
  6. customPurification by flash chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-7c2ef2e7d7584d469c1259c61e875f90
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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