Triethylamine → N-{4-[2-(4-formylphenoxy)ethyl]phenyl}methanesulfonamide

HRID 1595498Notes

Reaction equation

HRID 1595498 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1.C(OCC)(=O)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH:22]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:10][CH:11]=2)=[CH:25][CH:24]=1)=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 217050034-[2-(4-Aminophenyl)ethoxy]benzaldehyde

Product 1

HCID 21704959N-{4-[2-(4-formylphenoxy)ethyl]phenyl}methanesulfonamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.75 g (64 mmole) triethylamine was added to 5 g (14,6 mmole) 4-[2-(4-aminophenyl)ethoxy]benzaldehyde x HCl (containing some ethyl acetate) in dichloromethane. 3.65 g (32 mmole) methanesulfonyl chloride was slowly added at 0° C., and the mixture was stirred over the weekend. A yellow precipitate was filtered off and the filtrate was washed with water. The organic phase was dried (sodium sulfate), filtered and the solvent was evaporated. The residue contained some triethylamine and therefore it was dissolved in dichloromethane and washed with 2 M hydrochloric acid and brine, dried and filtered and the solvent was evaporated to give 1.6 g (yield 34%) of N-{4-[2-(4-formylphenoxy)ethyl]phenyl}methanesulfonamide as a yellow powder.

Workup

  1. filtrationA yellow precipitate was filtered off
  2. washthe filtrate was washed with water
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. dissolutionit was dissolved in dichloromethane
  7. washwashed with 2 M hydrochloric acid and brine
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4bdc8e2151f94c01a57e9a00352e2cf1
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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