Benzoyl chloride → HCID 15407873, compound

HRID 1417071Notes

Reaction equation

HRID 1417071 reaction equation
C([NH:4]C(C)C)(C)C.C([Li])CCC.[C:13]([C:15]1[CH:31]=[CH:30][C:18]([C:19]([N:21]([CH3:29])[CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=O)=[CH:17][CH:16]=1)#[N:14].[C:32](Cl)(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[NH4+].[Cl-]>C1COCC1>[C:13]([C:15]1[CH:31]=[CH:30][C:18]([C:19]2[N:21]([CH3:29])[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:4]=2)=[CH:17][CH:16]=1)#[N:14]

Participants

7

Reactant 5

HCID 7412Benzoyl chlorideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 15407881HCID 15407881, compoundHCID 178418339Butyllithium

Product 1

HCID 15407873HCID 15407873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Cyano-N-[N"-a-dibenzoyl-1,4-dihydropyridyl-methylenyl]-N-methylbenzarmide--To a solution of diisopropylamine (2.8 mL, 20 mmol) in THF at -78° C. was added n-butyllithium (6.7 mL of 2.5M solution, 17 mmol). To the resulting mixture was added a solution of 4-cyano-N-methyl-N-(4-picolyl)benzamide (3.5 g, 14 mmol) in THF. The resulting dark purple solution was stirred at -78° C. for 10 min, at which time benzoyl chloride (4.1 mL, 35 mmol) was added. The mixture was warmed to room temperature over 30 min, then poured into aqueous NH4Cl. The mixture was extracted with Et2O, and the organic extract was evaporated under reduced pressure. The residue was triturated with Et2O to provide an orange solid which was washed sparingly with acetone and copiously with Et2O. The title compound was obtained as a bright yellow solid (1.6 g, 25%): 1H NMR (CDCl3): d 7.81-7.09 (m, 16H); 6.49 (m, 2H); 3.32 (s, 3H).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with Et2O
  3. extractionthe organic extract
  4. customwas evaporated under reduced pressure
  5. customThe residue was triturated with Et2O
  6. customto provide an orange solid which
  7. washwas washed sparingly with acetone and copiously with Et2O

Sources & evidence

ORD record
ord-30060b9fda54413ea3f7f5a7b52775d9
Source dataset
uspto-grants-1999_06
Patent number
US05916891

Reaction notes

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