1,2-Dichloroethane → 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-N,N-dimethyl-isonicotinamide

HRID 1945447Notes

Reaction equation

HRID 1945447 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([OH:14])=O)=[O:7].[CH3:23][NH:24][CH3:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([N:24]([CH3:25])[CH3:23])=[O:14])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 580013332-[2-(2,4-Dichloro-phenoxy)acetylamino]-isonicotinic acid

Product 1

HCID 580013322-[2-(2,4-dichloro-phenoxy)-acetylamino]-N,N-dimethyl-isonicotinamideYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid (100.0 mg, 0.31 mmol), dimethylamine (0.24 ml, 0.47 mmol, in 2.0 M tetrahydrofuran), EDC (90.1 mg, 0.47 mmol) and HOBt (63.5 mg, 0.47 mmol) in DMF 4 ml was added DIPEA (60.8 mg, 0.08 ml, 0.47 mmol), and stirred. Reaction mixture was then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by preparative-TLC (n-Hexane:EtoAC:MeOH=6:3:1) to afford 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-N,N-dimethyl-isonicotinamide as a yellow solid (52.9 mg, 46.5% yield).

Workup

  1. customReaction mixture
  2. customwas then partitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative-TLC (n-Hexane:EtoAC:MeOH=6:3:1)

Sources & evidence

ORD record
ord-a1ae2a334bd94416801d33151cfe3302
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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