Sodium hydride → HCID 178422610, compound

HRID 1181034Notes

Reaction equation

HRID 1181034 reaction equation
[H-].[Na+].S([NH:13][N:14]=[C:15]([CH2:17]P(OCC)(OCC)=O)[CH3:16])(C1C=CC(C)=CC=1)(=O)=O.[C:26]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1>C1COCC1.CN(C=O)C>[C:26]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][C:29]([C:32]2[NH:13][N:14]=[C:15]([CH3:17])[CH:16]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 73733161HCID 73733161, compound

Product 1

HCID 178422610HCID 178422610, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
2.5 °C

Procedure

To a stirred mixture of NaH (1.98 g, 0.049 mol, 60% oil dispersion) in dry THF (30 mL) was added a suspension of diethoxyphosphorylacetone tosyl hydrazone (8.97 g, 0.024 mol; N Almirante Syn. Lett. 1999, 302.) in a mixture of THF (35 mL) and DMF (5.0 mL) dropwise over 15 min. The yellow suspension was stirred at 0-5° C. for 30 min and was treated with a 4-biphenyl carboxaldehyde (3.10 g, 0.0169 mol) in dry THF (30 mL) at 0-5° C. over 15 min. The orange solution was heated and stirred at reflux for 4 h and stirred at ambient temperature overnight. The mixture was poured into 5% aq. NaH2PO4 (350 mL) and extracted with EtOAc (2×200 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered, and concentrated to a yellow semi-solid. This material was triturated with hot EtOAc (20 mL) and filtered. The solid was washed with EtOAc (2×10 mL) and dried under high vacuum to give the title compound (2.61 g, 47%): HRMS Calculated for C16H15N2: m/z 235.1235. Found: 235.1230.

Workup

  1. additionwas added
  2. temperatureThe orange solution was heated
  3. stirringstirred
  4. temperatureat reflux for 4 h
  5. stirringstirred at ambient temperature overnight
  6. extractionextracted with EtOAc (2×200 mL)
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to a yellow semi-solid
  11. customThis material was triturated with hot EtOAc (20 mL)
  12. filtrationfiltered
  13. washThe solid was washed with EtOAc (2×10 mL)
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-97e06057fde6423d95a2fd249d7635ef
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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