Potassium Carbonate → HCID 22257137, compound

HRID 1611461Notes

Reaction equation

HRID 1611461 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Cl:22][C:23](Cl)([Cl:27])[CH2:24][CH2:25]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:22][C:23]([Cl:27])=[CH:24][CH2:25][O:20][C:18]1[CH:19]=[C:2]([Cl:1])[C:3]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[C:16]([Cl:21])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140561,1,1,3-TetrachloropropaneHCID 22257125HCID 22257125, compound

Product 1

HCID 22257137HCID 22257137, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Step D of Example 1, using 3.5 grams (0.0104 mole) of N-[3-(2,6-dichloro-4-hydroxyphenoxy)propyl](tert-butoxy)carboxamide, 2.3 grams (0.0125 mole) of 1,1,1,3-tetrachloropropane and 3.4 grams (0.0250 mole) of potassium carbonate in DMF. The crude product was purified with column chromatography on silica gel using a mixture of 1:3 hexane and methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 2.6 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 1
  2. customThe crude product was purified with column chromatography on silica gel using
  3. additiona mixture of 1:3 hexane and methylene chloride as an eluant
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61fdd69a34be42c3b52f8a5817c4e9b7
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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