3-Aminobenzamide → 3-[2-(4-Iodo-phenoxy)acetyl-amino]-benzamide

HRID 1945389Notes

Reaction equation

HRID 1945389 reaction equation
[I:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH2:19])=[O:18].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])=[O:10])=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 16453-AminobenzamideHCID 746584-Iodophenoxyacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 248112093-[2-(4-Iodo-phenoxy)acetyl-amino]-benzamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (4-iodo-phenoxy)acetic acid (83.5 mg, 0.3 mmol), 3-amino-benzamide (61.3 mg, 0.45 mmol), N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (86.3 mg, 0.45 mmol) and 1-hydroxybenzotriazole (HOBt) (61.3 mg, 0.45 mmol) in DMF (3 ml) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.08 ml, 0.45 mmol). The mire was stirred overnight, and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2CH2:MeOH=6:1) to give 3-[2-(4-iodo-phenoxy)acetyl-amino]-benzamide as a white solid (105.1 mg, 88.4% yield).

Workup

  1. distillationredistilled (DIPEA) (0.08 ml, 0.45 mmol)
  2. custompartitioned between ethyl acetate and water
  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 (CH2CH2:MeOH=6:1)

Sources & evidence

ORD record
ord-22e1170d8cfd4a6c8825cfbc2ed79f3b
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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