Réaction #2388153

ord-fa067522dd3944488487a7fb25541f81

Équation de réaction

CC(C)(C)N
tert-butylamine
COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)Cl
methyl 2-chlorosulfonyl-4-nitro-benzoate
→
COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)NC(C)(C)C
N-tert.-butyl-2-methoxycarbonyl-5-nitro-benzenesulfonamide

Réactifs

CC(C)(C)N
tert-butylamine
COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)Cl
methyl 2-chlorosulfonyl-4-nitro-benzoate

Réactifs

Aucun

Solvants

CCOC(C)=O
ethyl acetate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    LavageAfter washing with dilute hydrochloric acid and water
  2. 2
    Séchagethe organic phase is dried over MgSO4
  3. 3
    Concentrationconcentrated
  4. 4
    ExtractionThe residue is extracted
  5. 5
    workup.STIRRINGby stirring with diisopropyl ether

Mode opératoire

206 g of tert-butylamine are added dropwise to a solution of 384 g of methyl 2-chlorosulfonyl-4-nitro-benzoate (Example b) in 1500 ml of ethyl acetate at 0° C. The reaction mixture is then allowed to warm up to room temperature and is stirred at this temperature for 1 hour. After washing with dilute hydrochloric acid and water, the organic phase is dried over MgSO4 and concentrated. The residue is extracted by stirring with diisopropyl ether; Yield of sulfonamide: 377.6 g; m.p.: 122-124° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06498253B1uspto-grants-2002_12