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

HRID 1868965Notes

Reaction equation

HRID 1868965 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-9e55a844a281457bb88f8d16aec0e1da
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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