Pyridine → 4-[(ethylsulfonyl)amino]benzoic acid

HRID 2073722Notes

Reaction equation

HRID 2073722 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.N1C=CC=CC=1.[CH2:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20]>C(Cl)Cl>[CH2:19]([S:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)(=[O:23])=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2337BenzocaineHCID 11667Ethanesulfonyl chloride

Product 1

HCID 15162614-[(ethylsulfonyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 16.5 g (0.1 mol) of ethyl 4-aminobenzoate and 16 g (0.2 mol) of pyridine in 200 mL of methylene chloride cooled to 0° C. add dropwise 13 g (0.1 mol) of ethanesulfonyl chloride. After the addition is complete stir the mixture at 20° C. for 4 hr. After this time extract the mixture with three 100 mL portions of 1N sodium hydroxide. Heat the basic extracts at reflux for 2 hr, cool to 0°-10° C. and carefully add 60 mL of concentrated hydrochloric acid. Collect the resulting precipitate to obtain the title compound.

Workup

  1. additionAfter the addition
  2. extractionAfter this time extract the mixture with three 100 mL portions of 1N sodium hydroxide
  3. temperatureHeat the basic extracts
  4. temperatureat reflux for 2 hr
  5. temperaturecool to 0°-10° C.
  6. customCollect the resulting precipitate

Sources & evidence

ORD record
ord-6ef24752c0274e68a2327c7ab7d2974a
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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