Water → HCID 20378385, compound

HRID 2051917Notes

Reaction equation

HRID 2051917 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.CS(O[CH2:18][CH:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:20])(=O)=O.CN(C)P(N(C)C)(N(C)C)=O.O>C(O)C>[O:21]([CH:19]([CH3:20])[CH2:18][NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 12296945HCID 12296945, compound

Product 1

HCID 20378385HCID 20378385, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 33 g of ethyl p-aminobenzoate, 0.10 mole of 2-phenoxy-1-propanol O-methanesulfonate and 80 ml of hexamethylphosphoramide is heated at 125° C. for 18 hours. The mixture is chilled, poured into water and extracted with ether. The ether extract is washed with water, dried over magnesium sulfate and concentrated under vacuum to an oil. The oil is combined with 250 ml of ethanol-water (9:1) and 20 g of potassium hydroxide and the mixture refluxed for 3.5 hours. The mixture is acidified with concentrated hydrochloric acid, diluted with water and extracted with chloroform. The chloroform extracts are washed with water, dried (magnesium sulfate) and concentrated under vacuum to give an oil. Ethanol is added and the mixture chilled and filtered to give the product, mp 140°-144° C. Recrystallization gives the product as crystals, mp 145°-147° C.

Workup

  1. temperatureThe mixture is chilled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum to an oil
  7. temperaturethe mixture refluxed for 3.5 hours
  8. additiondiluted with water
  9. extractionextracted with chloroform
  10. washThe chloroform extracts are washed with water
  11. dry with materialdried (magnesium sulfate)
  12. concentrationconcentrated under vacuum
  13. customto give an oil
  14. temperaturethe mixture chilled
  15. filtrationfiltered
  16. customto give the product, mp 140°-144° C
  17. customRecrystallization

Sources & evidence

ORD record
ord-f1fbfd889a5249c8a216bb1f822ad49d
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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