(2,4-Dichlorophenoxy)Acetic Acid → Methyl 4-{[(2,4-dichlorophenoxy)acetyl]amino}benzoate

HRID 1945375Notes

Reaction equation

HRID 1945375 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=2[Cl:1])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 12082Methyl 4-aminobenzoateHCID 2724699PyBOP

Product 1

HCID 4572426Methyl 4-{[(2,4-dichlorophenoxy)acetyl]amino}benzoateYield 95.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The mixture of (2,4-dichloro-phenoxy)-acetic acid (110.5 mg, 0.5 mmol), 4-aminobenzoic acid methyl ester (151.2 mg, 1.0 mmol), 4-dimethylaminopyridine (122.7 mg, 1.0 mmol) and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (pybop) (520.3 mg, 1.0 mmol) in DMF (8.0 mL) was stirred overnight and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1) to give 4-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (169.6 mg, 95.8% yield).

Workup

  1. custompartitioned between ethyl acetate and 10% HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)

Sources & evidence

ORD record
ord-3d79620575f74b9f89a06e7ba5b947bf
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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