Dimethylamine → 2-(4-Chloro-phenoxy)-N,N-dimethyl-nicotinamide

HRID 1246631Notes

Reaction equation

HRID 1246631 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[N:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](Cl)=[O:13])=[CH:7][CH:6]=1>O.C1C=CC=CC=1>[Cl:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[N:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([N:2]([CH3:3])[CH3:1])=[O:13])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 27748982-(4-Chlorophenoxy)pyridine-3-carbonyl chloride

Product 1

HCID 5420852-(4-Chloro-phenoxy)-N,N-dimethyl-nicotinamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

To a rapidly stirred mixture of 10 mL of benzene and dimethylamine (2.6 mL of a 40% solution) was added a slurry of 2-(4-chlorophenoxy)nicotinoyl chloride (0.536 g, 2 mmol, Maybridge Chemical Co.) over 5 min. The biphasic mixture was stirred at room temperature for 18 h and then diluted with water and benzene. The aqueous layer was further extracted with benzene and the organic layers were combined and washed (brine, water), dried (Na2SO4) and concentrated in vacuo to produce the product as a pale yellow oil (0.432 g); δH (CDCl3, 400 MHz) 8.14 (dd, 1H), 7.72 (dd, 1H), 7.33 (m, 2H), 7.03 (m, 3H), 3.12 (s, 3H), 2.99 (s, 3H); MS m/z279, 277 (MH+).

Workup

  1. extractionThe aqueous layer was further extracted with benzene
  2. washwashed (brine, water)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10ac4c4888664983b3e7ebe9c016174b
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

Loading…