Hydrochloric Acid → Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

HRID 1842983Notes

Reaction equation

HRID 1842983 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>CN(C=O)C.C(O)(C(F)(F)F)=O.[Mn]>[CH3:11][S:8]([NH:7][CH2:6][C:5]1[CH:12]=[CH:13][C:2]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10807Ethyl 2-chloropropionateHCID 19027423N-[(4-bromophenyl)methyl]methanesulfonamide

Product 1

HCID 70816013Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 23930ManganeseCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-(4-bromobenzyl)methanesulfonamide (675 mg, 2.555 mmol) in DMF were added ethyl 2-chloropropionate (0.42 mL), manganese (280 mg) and (2,2′-bipyridine)nickel(II)-dibromide (NiBr2bipy) (67 mg, 0.17885 mmol). TFA (1-2 drops) was added. The reaction mixture was stirred for 36 h at 60° C. After cooling down to room temperature, the mixture was hydrolyzed by 1N HCl and extracted with diethyl ether. The organic layer was dried (MgSO4) and filtered. The solvent was removed in vacuo. The crude product was purified by CC. Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 mg) was obtained.

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-5ea7c1f48b6941bf97aadf072c0b3928
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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