Benzoyl chloride → HCID 15887617, compound

HRID 377104Notes

Reaction equation

HRID 377104 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][N:8]=2)=[C:4]([CH3:16])[CH:3]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:9][N:8]=2)=[C:4]([CH3:16])[CH:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 28001436-(4-chloro-2-methylphenoxy)pyridin-3-amine

Product 1

HCID 15887617HCID 15887617, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

2-(4-Chloro-2-methyl-phenoxy)-5-aminopyridine (211 mg, 0.90 mmol) was dissolved in methylene chloride (2.7 mL) then treated with triethylamine (0.19 mL, 1.35 mmol) followed by benzoyl chloride (0.13 mL, 1.12 mmol). The reaction mixture was stirred for 3 hours at 22° C. then saturated aqueous NaHCO3 was added and the mixture was stirred for another hour. The organic layer was separated and washed 2× with 6% aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel using 1:1 ethyl acetate/hexane as eluent. The product was recovered as a white solid. MS (m/z): 338/340 (M+H)+ ; C19H15N2O2Cl requires 338.8.

Workup

  1. stirringthe mixture was stirred for another hour
  2. customThe organic layer was separated
  3. washwashed 2× with 6% aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel using 1:1 ethyl acetate/hexane as eluent
  7. customThe product was recovered as a white solid

Sources & evidence

ORD record
ord-8133102d185e4025aadacb41a5fe910f
Source dataset
uspto-grants-2000_02
Patent number
US06022884

Reaction notes

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