Potassium Carbonate → HCID 85901699, compound

HRID 1863270Notes

Reaction equation

HRID 1863270 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[CH3:8].[CH2:27](I)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)P(N(C)C)(N(C)C)=O.O>[CH2:7]([O:9][C:10](=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([NH:25][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 20392571HCID 20392571, compound

Product 1

HCID 85901699HCID 85901699, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
50 °C

Procedure

A slurry of 3.45 g of anhydrous potassium carbonate in 50 ml of hexamethylphosphoramide (HMPA) containing 6.8 g of ethyl[p-(p-aminophenoxy)phenyl]acetate is heated to 50° C. A solution of 6 g of n-octyliodide in 10 ml of HMPA is added over 2 hours. The heating is continued for 24 hours. The mixture is diluted with 100 ml of H2O and extracted with two 100 ml portions of ether. The combined extracts are washed with two 100 ml portions of H2O, 100 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent at reduced pressure affords a brown liquid, which yields, after silica gel chromatography (benzene, then CHCl3) and bulb-to-bulb distillation of the CHCl3 eluate, a pale yellow oil, b.p. 194° @ 0.05 mm.

Workup

  1. extractionextracted with two 100 ml portions of ether
  2. washThe combined extracts are washed with two 100 ml portions of H2O, 100 ml of saturated brine
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent at reduced pressure
  5. customaffords a brown liquid, which
  6. customyields
  7. distillationafter silica gel chromatography (benzene, then CHCl3) and bulb-to-bulb distillation of the CHCl3 eluate

Sources & evidence

ORD record
ord-51286894420648c4a48e028ed5f46807
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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