Hydrochloric Acid → Ethyl 2-(2-nitrobenzenesulfonamido)acetate

HRID 1244793Notes

Reaction equation

HRID 1244793 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].Cl>C(Cl)Cl>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 3454399Ethyl 2-(2-nitrobenzenesulfonamido)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of glycine ethyl ester hydrochloride (9.45 g) in methylene chloride (100 ml) were added triethylamine (18.9 ml) and 2-nitrobenzenesulfonyl chloride (10.0 g) in succession under cooling with ice and the mixture was stirred at room temperature for 2 days. To the reaction mixture was added 1N hydrochloric acid under cooling with ice, followed by extraction with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate, then saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the precipitated crystals were washed with a mixed solvent of n-hexane and diethyl ether, collected by filtration and air-dried to obtain the title compound (10.8 g).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionfollowed by extraction with methylene chloride
  4. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialsaturated sodium chloride solution, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe precipitated crystals were washed with a mixed solvent of n-hexane and diethyl ether
  8. filtrationcollected by filtration
  9. customair-dried

Sources & evidence

ORD record
ord-9e21e33563f543c28bc09e47d4b11db5
Source dataset
uspto-grants-2006_10
Patent number
US07122662B2

Reaction notes

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