Pyridine → HCID 19863365, compound

HRID 1164946Notes

Reaction equation

HRID 1164946 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[O:24]=[C:25]([CH2:31][CH3:32])[CH2:26][CH2:27][C:28](Cl)=[O:29].S(Cl)(Cl)=O.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:28](=[O:29])[CH2:27][CH2:26][C:25](=[O:24])[CH2:31][CH3:32])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 65578Oxalyl chlorideHCID 84342p-Nitro-N-benzylanilineHCID 13839458HCID 13839458, compound

Product 1

HCID 19863365HCID 19863365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 22.8 g (0.1 mol) of 4-nitro-N-(phenylmethyl)benzenamine and 7.9 g (0.1 mol) of pyridine in 150 mL of methylene chloride cooled to 0° C. add slowly a solution of 16.3 g (0.11 mol) of 4-oxohexanoyl chloride (prepared from the acid and thionyl chloride or oxalyl chloride). When the addition is complete stir the solution and allow to warm slowly to room temperature. Follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction wash the solution with two 25 mL portions of 5% hydrochloric acid solution, two 25 mL portions of 5% sodium carbonate solution and 50 mL of saturated sodium chloride solution. Dry the organic phase over anhydrous sodium sulfate. Remove the drying agent by filtration and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. additionWhen the addition
  2. customthe progress of the reaction by thin-layer chromatography on silica gel
  3. washAt the completion of the reaction wash the solution with two 25 mL portions of 5% hydrochloric acid solution, two 25 mL portions of 5% sodium carbonate solution and 50 mL of saturated sodium chloride solution
  4. dry with materialDry the organic phase over anhydrous sodium sulfate
  5. customRemove the drying agent
  6. filtrationby filtration
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-c2d259dc9d3745dfa760b9f1a985162b
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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