N-Ethylaniline → 2-[Ethyl(phenyl)amino]ethane-1-sulfonyl fluoride

HRID 893882Notes

Reaction equation

HRID 893882 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.Cl[CH2:18][CH2:19][S:20]([F:23])(=[O:22])=[O:21]>C1C=CC=CC=1>[F:23][S:20]([CH2:19][CH2:18][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 8471TriethylamineHCID 69807Ethanesulfonyl fluoride, 2-chloro-

Product 1

HCID 211616872-[Ethyl(phenyl)amino]ethane-1-sulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-Ethylaniline (48.4 g 0.4 m), triethylamine (40.4 g 0.4 m) and benzene (100 ml) are stirred together at room temperature and 2-chloroethanesulfonyl fluoride (58.6 g, 0.4 m) is added dropwise. The reaction mixture is heated at reflux for 1.5 hr. after the addition is completed. The reaction mixture is cooled and filtered to remove any insoluble salts, and the benzene is removed by distillation. The crude product is drowned into hexane (150 ml) and purified by filtration and washing with hexane. The product melts at 48°-50° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 1.5 hr
  3. additionafter the addition
  4. temperatureThe reaction mixture is cooled
  5. filtrationfiltered
  6. customto remove any insoluble salts
  7. customthe benzene is removed by distillation
  8. filtrationpurified by filtration
  9. washwashing with hexane

Sources & evidence

ORD record
ord-81e06920a49f4661a6f671681dad4846
Source dataset
uspto-grants-1981_08
Patent number
US04282144

Reaction notes

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