Pyridine → N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamide

HRID 2094783

Reaction equation

HRID 2094783 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH:15][CH3:16])=[O:14])[CH:8]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:25][C:26]([Cl:31])([Cl:30])[C:27](Cl)=[O:28]>ClCCl>[CH3:16][NH:15][C:13](=[O:14])[C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([NH:1][C:27](=[O:28])[C:26]([Cl:31])([Cl:30])[Cl:25])=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 166551294-(4-Aminophenoxy)-N-methylpicolinamide

Product 1

HCID 68728447N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamideYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The clear solution of 4-(4-aminophenoxy)-N-methylpicolinamide (100 g, 0.411 mol) in dichloromethane (100 ml) was cooled to 0° C. to −5° C. and pyridine (83 ml, 1.02 mol) was added in one lot to the reaction mass. It was then agitated at same temperature for 15 minutes and a solution of trichloroacetyl chloride (60 ml, 0.535 mol) in dichloromethane (500 ml) was added dropwise maintaining temperature of the reaction mass below 0° C. The reaction mass was then stirred for 2-3 hours below 0° C. and quenched with water (500 ml) below 5° C. The organic phase was then separated and aqueous layer was reextracted with dichloromethane. The combined dichloromethane layer was washed with water, dried over sodium sulfate and evaporated under vacuum to obtain (72 g) of the desired product.

Workup

  1. temperaturemaintaining temperature of the reaction mass below 0° C
  2. stirringThe reaction mass was then stirred for 2-3 hours below 0° C.
  3. customquenched with water (500 ml) below 5° C
  4. customThe organic phase was then separated
  5. washThe combined dichloromethane layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-a2caaba5c91f48c2b3750f86f2b60b7f
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Linked notes

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