Benzocaine → 4-{[2-(4-Fluorophenyl)ethyl]amino}benzoic acid

HRID 2052503Notes

Reaction equation

HRID 2052503 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=1.[I-].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 4875Potassium IodideHCID 12679HexamethylphosphoramideHCID 676221-(2-Chloroethyl)-4-fluorobenzene

Product 1

HCID 130796804-{[2-(4-Fluorophenyl)ethyl]amino}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.8 g. of 1-(2-chloroethyl)-4-fluorobenzene, 33 g. of ethyl p-aminobenzoate, 16.6 g. of potassium iodide and 100 ml. of hexamethylphosphoramide is heated at 95° C. for 15 hours. The mixture is poured into water and extracted with ether. The ether extracts are washed with water, dried over magnesium sulfate and concentrated in vacuo to an oil. To the oil is added 200 ml. of ethanol-water (9:1) and 21 g. of potassium hydroxide and the mixture is refluxed for 3.5 hours. The mixture is acidified with concentrated hydrochloric acid, diluted with water, cooled and filtered to give gray crystals. Recrystallization from ethanol gives light gray crystals, m.p. 161°-163° C.

Workup

  1. additionA mixture of 15.8 g
  2. extractionextracted with ether
  3. washThe ether extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oil
  6. additionTo the oil is added 200 ml
  7. temperatureof potassium hydroxide and the mixture is refluxed for 3.5 hours
  8. additiondiluted with water
  9. temperaturecooled
  10. filtrationfiltered
  11. customto give gray crystals
  12. customRecrystallization from ethanol
  13. customgives light gray crystals, m.p. 161°-163° C.

Sources & evidence

ORD record
ord-85bae272d5f54f1ea7d908f75b33abad
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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