Potassium Carbonate → 1-[p-(N',N'-dimethylureido)-phenoxy]-2-hydroxy-3-isopropylaminopropane

HRID 1581069Notes

Reaction equation

HRID 1581069 reaction equation
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH:14]([NH:17][CH2:18][CH:19]([OH:22])[CH2:20]Cl)([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][CH:19]([OH:22])[CH2:18][NH:17][CH:14]([CH3:16])[CH3:15])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3014146Urea, N'-(4-hydroxyphenyl)-N,N-dimethyl-HCID 126246123-Isopropylamino-2-hydroxy-1-chloropropane

Product 1

HCID 126663201-[p-(N',N'-dimethylureido)-phenoxy]-2-hydroxy-3-isopropylaminopropane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 20 g of p-(N',N'-dimethylureido)-phenol, 15 g of 3-isopropylamino-2-hydroxy-1-chloropropane, and 20 g of finely ground potassium carbonate in 250 ml of acetone is stirred at 50° for 5 hours. The solid part of the mixture is filtered off and the acetone solution is evaporated in a vacuum. The residue is dissolved in 100 ml of 2N hydrochloric acid, the undissolved part is filtered off and the remaining mixture is extracted with methylene chloride. The aqueous phase is rendered alkaline by adding 2N sodium hydroxide solution and is extracted with methylene chloride. After the evaporation of the solvent, 1-[p-(N',N'-dimethylureido)-phenoxy]-2-hydroxy-3-isopropylaminopropane is isolated which melts at 138°-139° after recrystallisation from benzene and has the formula ##SPC6##

Workup

  1. filtrationThe solid part of the mixture is filtered off
  2. customthe acetone solution is evaporated in a vacuum
  3. dissolutionThe residue is dissolved in 100 ml of 2N hydrochloric acid
  4. filtrationthe undissolved part is filtered off
  5. extractionthe remaining mixture is extracted with methylene chloride
  6. additionby adding 2N sodium hydroxide solution
  7. extractionis extracted with methylene chloride
  8. customAfter the evaporation of the solvent

Sources & evidence

ORD record
ord-163c6c30691d48c2a5e9791940fc7bb3
Source dataset
uspto-grants-1976_01
Patent number
US03935259

Reaction notes

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