Phenol → HCID 86583809, compound

HRID 1387527Notes

Reaction equation

HRID 1387527 reaction equation
[C:1]1([NH:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1(O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O.C(OCC)C>[C:1]1([NH:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:11]([O:13][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 18626155HCID 18626155, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 86583809HCID 86583809, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

N,N′-Carbonyldiimidazole (0.41 g, 2.5 mmol) was added to a stirred solution of 3-(phenylamino)-4-methoxybenzoic acid (0.6 g, 2.5 mmol) in dimethylformamide (15 mL) under an inert atmosphere. After 30 minutes, the solution was heated to 50° C. for 1 hour, then phenol (0.24 g, 2.6 mmol) was added followed by diazabicycloundecene (0.40 g, 2.6 mmol) and heating at 50° C. was continued for 20 more hours. The mixture was allowed to cool and was then diluted with diethyl ether (100 mL) and washed successively with 2N HCl, water, 0.5N K2CO3, and saturated brine then dried over MgSO4. The solvent was removed under reduced pressure, and the residue was chromatographed on a column of silica gel in ethyl acetate to afford the product (0.27 g); m.p. 130-131° C. after recrystallization from acetonitrile.

Workup

  1. temperatureheating at 50° C.
  2. temperatureto cool
  3. washwashed successively with 2N HCl, water, 0.5N K2CO3, and saturated brine
  4. dry with materialthen dried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed on a column of silica gel in ethyl acetate

Sources & evidence

ORD record
ord-432e2d04b9754bda85504a4deba96859
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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