2,4,5-Trichlorophenol → HCID 67852021, compound

HRID 1742744Notes

Reaction equation

HRID 1742744 reaction equation
[C:1]([C:8]([CH2:23][CH2:24][NH2:25])=[C:9]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([Cl:34])=[CH:29][C:28]=1O.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([Cl:34])=[CH:29][C:28]=1[O:11][C:10](=[O:12])[C:9]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[C:8]([C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[CH2:23][CH2:24][NH2:25]

Participants

5

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67852055HCID 67852055, compound

Product 1

HCID 67852021HCID 67852021, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acid in Example 20a (195 mg, 0.57 mmol) in 8 mL anhydrous methylene chloride was treated with 2,4,5-trichlorophenol (112 mg, 0.57 mmol) and EDCI (160 mg, 0.85 mmol). The reaction mixture was stirred for 24 hours at ambient temperature under nitrogen atmosphere. The mixture was washed with 10% citric acid and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated to yield a residue that was purified by flash chromatography on silica gel. Elution with EtOAc/hexane (1/5~1/1, v/v, with 1% HOAc) afforded the title compound (158 mg, 54% yield) as an oil: 1H NMR (CDCl3, 60 MHz) δ1.45 (s, 9H), 2.58 (q, 2H), 3.28 (q, 2H), 3.85 (q, 2H), 4.80 (br, 1H), 7.2 (s, 1H), 7.5 (s, 1H), 6.8-7.8 (m, 6H), 10.1 (br, 1H).

Workup

  1. washThe mixture was washed with 10% citric acid and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto yield a residue that
  5. customwas purified by flash chromatography on silica gel
  6. washElution with EtOAc/hexane (1/5~1/1, v/v, with 1% HOAc)

Sources & evidence

ORD record
ord-6f994c5783ab499fb3eca6e896340f2e
Source dataset
uspto-grants-1994_08
Patent number
US05340802

Reaction notes

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