Benzoyl chloride → HCID 57826353, compound

HRID 1665852Notes

Reaction equation

HRID 1665852 reaction equation
[C-:1]#[N:2].[Na+].[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.C(Cl)Cl.C(OCC)(=O)C>[C:1]([CH:10]([O:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]1[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=1)#[N:2]

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 8929Sodium CyanideHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 57826353HCID 57826353, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium cyanide (1.96 g, 40 mmol) and benzyltridimethylammonium chloride (0.3 g, 1.3 mmol) in 7.5 mL of water was slowly added a solution of 3-pyridinecarboxaldehyde (0.88 mL, 9.3 mmol) in 15 mL of methylene chloride at 0° C. The resulting reaction solution was stirred at 0° C. for 15 min, and then benzoyl chloride (1.16 mL, 10 mmol) was additionally added thereto. After addition was complete, the reaction solution was elevated to room temperature and further stirred for 3 hours. After the reaction was complete, the reaction materials was diluted with 50 mL of ethyl acetate and 50 mL of water to dissolve salts, followed by separation of layers. The obtained organic layer was successively washed twice with 50 mL of a brine solution. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel column chromatography, to give 1.95 g (yield: 95%) of benzoic acid cyano-pyridin-3-yl-methyl ester of the following formula.

Workup

  1. customThe resulting reaction solution
  2. additionAfter addition
  3. customwas elevated to room temperature
  4. stirringfurther stirred for 3 hours
  5. dissolutionto dissolve salts
  6. customfollowed by separation of layers
  7. washThe obtained organic layer was successively washed twice with 50 mL of a brine solution
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2ea1ce7d9cd5458e87d5146f9d03237f
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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