Benzoyl chloride → HCID 87497032, compound

HRID 1948832Notes

Reaction equation

HRID 1948832 reaction equation
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C#N.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:21]([N:23](CC)CC)C>C(Cl)Cl>[C:12]([O:1]/[N:2]=[CH:3]/[C:6]1([C:21]#[N:23])[CH:7]=[CH:8][CH:9]=[CH:10][CH2:11]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 699982-(Hydroxyimino)-2-phenylacetonitrile

Product 1

HCID 87497032HCID 87497032, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 2-hydroxyimino-2-phenylacetonitrile (1.0 g, 6.84 mmol) in CH2Cl2 (30 ml), benzoylchloride (1.02 ml, 8.89 mmol) was slowly added at 0° C. under the presence of triethylamine (1.24 ml, 8.89 mmol). After stirring reaction solution for 1 hour, the reaction was quenched by 1 N hydrochloric acid and the reaction solution was extracted with dichloromethane. A pure compound of (E)-1-cyano-benzaldehyde O-benzoyloxime (14) (1.30 g, 81%) was obtained by separating the residue with silica gel column chromatography.

Workup

  1. customreaction solution for 1 hour
  2. customthe reaction was quenched by 1 N hydrochloric acid
  3. extractionthe reaction solution was extracted with dichloromethane

Sources & evidence

ORD record
ord-3fdf82aa80c04cf8bdcf3d2cbc410a68
Source dataset
uspto-grants-2013_03
Patent number
US08399662B2

Reaction notes

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