Potassium Carbonate → HCID 22257126, compound

HRID 1611459Notes

Reaction equation

HRID 1611459 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[OH:17].[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28]Br)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[O:17][CH2:28][CH2:27][CH2:26][NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 22257126HCID 22257126, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.69 grams (0.010 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound), 2.38 grams (0.010 mole) of (tert-butoxy)-N-(3-bromopropyl)carboxamide (commercially available) and 1.52 grams (0.011 mole) of potassium carbonate in 40 mL of DMF was stirred at ambient temperature during a four-day period. After this time the reaction mixture was shaken in diethyl ether and water, and the separated organic layer was washed with one portion of water and with one portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 4.15 grams of the subject compound.

Workup

  1. washwater, and the separated organic layer was washed with one portion of water and with one portion of an aqueous solution saturated with sodium chloride
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c094617b53646e2bc4c464955a94763
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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