(2,4-Dichlorophenoxy)Acetic Acid → HCID 1019273, compound

HRID 1945374Notes

Reaction equation

HRID 1945374 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][CH:20]=[CH:19][C:18]=1[NH2:23].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:6](=[O:8])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 8635Methyl AnthranilateHCID 81531DiisopropylethylamineHCID 2724699PyBOP

Product 1

HCID 1019273HCID 1019273, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (2,4-dichloro-phenoxy)-acetic acid (110.6 mg, 0.5 mmol), 2-aminobenzoic acid methyl ester (151.2 mg, 1.0 mmol), and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (pybop) (520.3 g, 1.0 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.17 mL, 1.0 mmol). The mixture 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 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (118.0 mg, 66.6% yield).

Workup

  1. distillationredistilled (DIPEA) (0.17 mL, 1.0 mmol)
  2. custompartitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)

Sources & evidence

ORD record
ord-a22a9d207fd94995aa9660d38f3cfc36
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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