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

HRID 1428713Notes

Reaction equation

HRID 1428713 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)C=O.FC(F)(F)C(O)=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 dimethylformamide were added ethyl 2-chloropropionate (0.42 mL), manganese (280 mg) and (2,2′-bipyridine)nickel(II)-dibromide (67 mg, 0.17885 mmol). Trifluoroacetic acid (2 drops) was added. The reaction mixture was stirred for 36 h at 60° C. After cooling down to room temperature, the mixture was hydrolysed by 1N HCl and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to obtain ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 mg).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-416544318e194d2bb5f564fc25217aea
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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