2-Chloro-4-fluorobenzaldehyde → HCID 10162886, compound

HRID 1791122Notes

Reaction equation

HRID 1791122 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[F:12][C:13]1[C:14]([C:20](=[NH:22])[NH2:21])=[N:15][CH:16]=[C:17]([F:19])[CH:18]=1.[N:23]1([CH2:29][C:30](=O)[CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C([O-])(=O)C.[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]1[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([CH2:29][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[NH:21][C:20]([C:14]2[C:13]([F:12])=[CH:18][C:17]([F:19])=[CH:16][N:15]=2)=[N:22]1

Participants

6

Reactant 4

HCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 15547736HCID 15547736, compoundHCID 220278403,5-Difluoropyridine-2-carboximidamide--hydrogen chloride (1/1)

Product 1

HCID 10162886HCID 10162886, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.38 g (2.4 mmol) of 2-chloro-4-fluorobenzaldehyde in 10 ml of isopropanol is heated together with 0.46 g (2.4 mmol) of the compound from Example VI, 0.48 g (2.4 mmol) of the compound from Example VIII and 0.24 g (2.88 mmol) of sodium acetate under reflux for 2 hours. The reaction mixture is concentrated, and the residue is taken up in dichloromethane and extracted with 2N hydrochloric acid. The aqueous phase is made alkaline with dilute ammonia solution and extracted with dichloromethane. The organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel with cyclohexane/ethyl acetate (20:1→10:1) as mobile phase, and the product is crystallized from diethyl ether.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture is concentrated
  3. extractionextracted with 2N hydrochloric acid
  4. extractionextracted with dichloromethane
  5. washThe organic phase is washed with aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel with cyclohexane/ethyl acetate (20:1→10:1) as mobile phase
  9. customthe product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-dce66c4685444307a96de17501db1619
Source dataset
uspto-grants-2006_07
Patent number
US07074784B2

Reaction notes

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