Potassium Carbonate → HCID 13497198, compound

HRID 903797Notes

Reaction equation

HRID 903797 reaction equation
Br[C:2]1[CH:20]=[CH:19][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:13][C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][O:4][C:3]3[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=3[NH:14][C:8]=2[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 23335110HCID 23335110, compound

Product 1

HCID 13497198HCID 13497198, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A suspension of 1.4 g. (0.004 moles) of (2-bromophenoxy)-(2-formamido-4-chlorophenoxy)-methane (m.p.: 98° to 100° C.), 0.6 g. (0.0042 moles) of potassium carbonate, 0.2 g. of copper powder and 12 ml. of Dowtherm(®) is heated up to 180° C. and is vigorously stirred at this temperature for 8 hours. The reaction mixture is filtered while hot, then the solvent is evaporated in vacuo. The remaining dark tar is hydrolyzed by boiling in a mixture of 20 ml. of ethanol and 2 ml. of a 20% aqueous sodium hydroxide solution for one hour. The reaction mixture is cooled and neutralized with a 37% aqueous hydrogen chloride solution. The solvent is evaporated and the brown solid residue is extracted with 10 ml. of hot benzene. Thereafter the solvent is eliminated and the residue is crystallized from benzine.

Workup

  1. additionA suspension of 1.4 g
  2. filtrationThe reaction mixture is filtered while hot, then the solvent
  3. customis evaporated in vacuo
  4. additionby boiling in a mixture of 20 ml
  5. waitof a 20% aqueous sodium hydroxide solution for one hour
  6. temperatureThe reaction mixture is cooled
  7. customThe solvent is evaporated
  8. extractionthe brown solid residue is extracted with 10 ml
  9. customthe residue is crystallized from benzine

Sources & evidence

ORD record
ord-a54024e14b04479d841c8de4b0763a26
Source dataset
uspto-grants-1980_10
Patent number
US04229350

Reaction notes

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