Pyridine → HCID 23092680, compound

HRID 2235443Notes

Reaction equation

HRID 2235443 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][C:6](=[O:14])[C:5]2([CH3:16])[CH3:15].N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:15][C:5]1([CH3:16])[C:4]2[C:8](=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([NH:1][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[CH:3]=2)[NH:7][C:6]1=[O:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 7477p-Anisoyl chlorideHCID 22162178HCID 22162178, compound

Product 1

HCID 23092680HCID 23092680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C1 (3.1 g) and dry pyridine (3.5 ml; 42 mmol) in dry CH2Cl2 (75 ml) is added 4-methoxy-benzoyl chloride (2.63 g; 15.4 mmol) over a period of 2 min. After addition the mixture is stirred at RT for 20 h. CHCl3 (200 ml) is added and the organic layer is washed with sodium hydroxide solution (0.5 N) and water, dried over MgSO4 and concentrated in vacuo. The crude material is triturated with boiling EtOH and the precipitate is collected by filtration (3.73 g).

Workup

  1. additionAfter addition the mixture
  2. washthe organic layer is washed with sodium hydroxide solution (0.5 N) and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material is triturated with boiling EtOH
  6. filtrationthe precipitate is collected by filtration (3.73 g)

Sources & evidence

ORD record
ord-d28c0b0577c44c73b5686cb6a54fe9e1
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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