Water → HCID 178511972, compound

HRID 75497Notes

Reaction equation

HRID 75497 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18](#[N:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1COCC1>[C:12]1([NH:11][C:18](=[NH:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115Aniline2×HCID 7505Benzonitrile2×HCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 178511972HCID 178511972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To NaHMDS (49 mL, 48.5 mmol, 1.0 M solution in THF) was added dropwise a solution of aniline (compound 11a, 4.5 mL, 48.5 mmol) in anhydrous THF (10 mL) under N2. After 20 min, a solution of benzonitrile (compound 21, 5.0 mL, 48.5 mmol) in anhydrous THF (10 mL) was slowly added. The reaction mixture was stirred for 12 hrs, poured into cold water and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f97fa1728e2a4102a53c8e3bce0e7797
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Reaction notes

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