Acetic Anhydride → N-[3-(6-Chloro-3-pyridazinyl)phenyl]acetamide

HRID 1906820Notes

Reaction equation

HRID 1906820 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 142802953-(6-Chloropyridazin-3-yl)aniline

Product 1

HCID 15595701N-[3-(6-Chloro-3-pyridazinyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 34.0 g of 3-(6-chloro-3-pyridazinyl)benzenamine, 18.8 ml of acetic anhydride, 28.7 ml of diisopropylethylamine and 750 ml of dichloromethane was stirred for 2.5 hrs. The solution was concentrated in vacuo to half of the original volume and 200 ml of hexane was added. The solution was filtered, affording 26.4 g of tan solid. The filtrate was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. The residue and the solid collected previously were combined and recrystallized from dichloromethane-acetone-hexane to give 35 g of tan crystals, mp 203°-205° C.

Workup

  1. concentrationThe solution was concentrated in vacuo to half of the original volume and 200 ml of hexane
  2. additionwas added
  3. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-0ab63932c7d849c2b1bcec63046c495a
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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