Hydrochloric Acid → [(2-Nitrophenylsulfonyl)amino]acetamide

HRID 2189346Notes

Reaction equation

HRID 2189346 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15].Cl>ClCCl>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:2][CH2:3][C:4]([NH2:6])=[O:5])(=[O:25])=[O:24])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 23078895[(2-Nitrophenylsulfonyl)amino]acetamideYield 27.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of glycinamide hydrochloride (0.11 g) and triethylamine (0.35 mL) in dichloromethane (3 mL) was added 2-nitrobenzenesulfonyl chloride (0.27 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1) to give the title compound (72 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1)

Sources & evidence

ORD record
ord-09f096c0bfa0430f9f60c08ba84733cb
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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