Tert-Butylamine → methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate

HRID 2300971Notes

Reaction equation

HRID 2300971 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([C:10]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8]>C(OCC)(=O)C>[C:1]([NH:5][S:7]([C:10]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:8])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 15240541Methyl 2-(chlorosulfonyl)-4-nitrobenzoate

Product 1

HCID 15240542methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. washAfter washing with dilute hydrochloric acid and water
  2. dry with materialthe organic phase is dried over MgSO4
  3. concentrationconcentrated
  4. extractionThe residue is extracted
  5. stirringby stirring with diisopropyl ether

Sources & evidence

ORD record
ord-fa067522dd3944488487a7fb25541f81
Source dataset
uspto-grants-2002_12
Patent number
US06498253B1

Reaction notes

Loading…