Pyridine → HCID 525044, compound

HRID 978098Notes

Reaction equation

HRID 978098 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].N1C=CC=CC=1.[C:16](Cl)(=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 72573,4-DichloroanilineHCID 69819Nonanoyl chloride

Product 1

HCID 525044HCID 525044, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3,4-Dichloroaniline, 13.7 g (0.084 mole), is dissolved in 200 ml dichloroethane, containing 25 ml pyridine. The solution is stirred at room temperature while nonanoyl chloride, 14.6 g (0.086 mole), is added slowly. The solution is stirred two hours. Excess pyridine is removed by washing the product with 4N hydrochloric acid. A crude product is crystallized from 95% ethanol. There is obtained N-(3,4-dichlorophenyl) nonanamide, a white crystalline solid, (M.P. 68.5-69.0%). Analysis shows 4.52% nitrogen and 23.26% chlorine as against calculated values of 4.63% and 23.48% respectively for C15H21Cl2NO.

Workup

  1. additionis added slowly
  2. customExcess pyridine is removed
  3. washby washing the product with 4N hydrochloric acid
  4. customA crude product is crystallized from 95% ethanol

Sources & evidence

ORD record
ord-da74bff30d134275a6714de76fac3812
Source dataset
uspto-grants-1987_05
Patent number
US04663353

Reaction notes

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