Triethylamine → Methyl 2-(2-nitrobenzenesulfonamido)acetate

HRID 2303352Notes

Reaction equation

HRID 2303352 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(CC)CC)C.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25])([O-:17])=[O:16]>ClCCl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][S:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N+:15]([O-:17])=[O:16])(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 743502Methyl 2-(2-nitrobenzenesulfonamido)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Glycine methyl ester hydrochloride (15.0 g) was dissolved in dichloromethane, and to the solution triethylamine (26.48 g) was added at 0° C. A solution of 2-nitrobenzenesulfonyl chloride (23.57 g) in dichloromethane (50 mL) was then gradually added dropwise. After the mixture was stirred at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The resultant mixture was washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crystals were recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe resultant mixture was washed with 2 M hydrochloric acid, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0d55c04c6ee34aff8cfdaeb4d1f92daa
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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