Potassium Carbonate → HCID 57085694, compound

HRID 903798Notes

Reaction equation

HRID 903798 reaction equation
Br[C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[O:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14]C=O.C(=O)([O-])[O-].[K+].[K+].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Cu]>[Cl:21][C:19]1[CH:20]=[CH:2][C:3]2[O:4][CH2:5][O:6][C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=3[NH:14][C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 23335116HCID 23335116, compound

Product 1

HCID 57085694HCID 57085694, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
20 °C

Procedure

A suspension of 4.1 g. (0.01 moles) of (2-bromo-4-chlorophenoxy)-(2-formamido-4-chlorophenoxy)-methane (m.p.: 148° to 149° C.), 2.1 g. (0.015 moles) of potassium carbonate, 0.5 g. (0.008 gatom) of copper powder and 30 ml. of Dowtherm(R)A is heated up to 190° C. and is kept at this temperature for 10 hours, while stirred vigorously. Thereafter the reaction mixture is filtered and from the filtrate the solvent is distilled off in vacuo. The remaining tar is boiled in a mixture of 45 ml. of ethanol and 4.5 ml. of a 20% aqueous sodium hydroxide solution for one hour, then cooled to 20° C. It is then neutralized with a 37% aqueous hydrochloric acid solution and the solvent is eliminated. The residue is extracted three times with 80 ml. portions each of hot cyclohexane, the combined extracts are decoloured while hot and the solvent is eliminated. Recrystallization of the crude product from carbon tetrachloride affords a white product weighing 0.6 g. (21.4%) and melting at 194° to 196° C.

Workup

  1. additionA suspension of 4.1 g
  2. filtrationThereafter the reaction mixture is filtered and from the filtrate the solvent
  3. distillationis distilled off in vacuo
  4. additionThe remaining tar is boiled in a mixture of 45 ml
  5. waitof a 20% aqueous sodium hydroxide solution for one hour
  6. extractionThe residue is extracted three times with 80 ml
  7. customRecrystallization of the crude product from carbon tetrachloride
  8. customaffords a white product

Sources & evidence

ORD record
ord-bfa4eda1617e461e9b4f3a8e05b645ed
Source dataset
uspto-grants-1980_10
Patent number
US04229350

Reaction notes

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