Tetrahydrofuran → HCID 59384155, compound

HRID 2266748Notes

Reaction equation

HRID 2266748 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[F:20])=[NH:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C([O:33][C:34]1C=C(C=[CH:39][CH:40]=1)N)C.FC1(C)C=CC(C#N)=CC1.[O:51]1CCCC1>[Cl-].[Na+].O.ClCCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:39]=[C:40]([C:34]([OH:33])=[O:51])[N:12]=[C:11]2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[F:20])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 121203-EthoxyanilineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 67297155HCID 67297155, compoundHCID 178466608HCID 178466608, compound

Product 1

HCID 59384155HCID 59384155, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-(3-Ethoxyphenyl)-2-fluoro-4-methylbenzenecarboximidamide To a solution of 2.2 ml (4.4 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide in 10 mL of tetrahydrofuran at ambient temperature was added 0.52 mL (4.0 mmol) of 3-ethoxyaniline and the resulting solution was stirred for 20 min. To this reaction mixture was added 0.54 g (4.0 mmol) of 4-fluoro-4-methylbenzonitrile. The resulting mixture was stirred at ambient temperature for 3 hrs and then poured into brine (25 mL) and dichloromethane (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (25 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as a pale green solid which was used without further purification.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 3 hrs
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3518d1f4eb6f4dd0a1fbcb0f8523d7f6
Source dataset
uspto-grants-2010_12
Patent number
US07858629B2

Reaction notes

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