Acetone → N-tert-Butyl-2-methoxy-4-nitro-benzenesulfonamide

HRID 970432Notes

Reaction equation

HRID 970432 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24].CC(C)=O>CC(C)=O.O>[C:23]([NH:27][S:12]([C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1])(=[O:14])=[O:13])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 3094582-Methoxy-4-nitrobenzenesulfonyl chloride

Product 1

HCID 47190031N-tert-Butyl-2-methoxy-4-nitro-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 5.0 g (19.9 mmol) of 2-methoxy-4-nitro-benzenesulfonyl chloride in acetone/water (60 ml/15 ml) is mixed at room temperature with 2.9 ml of triethylamine and 2.2 ml of tert.-butylamine. After 5 hours, the acetone is drawn off, and the residue is extracted from ethyl acetate. The combined organic phases are washed with dilute HCl solution and saturated NaCl solution and then filtered through a Whatman filter and concentrated by evaporation. The crude product that is obtained is recrystallized from ethyl acetate. 4.2 g (14.6 mmol, corresponding to 73% of theory) of the product is obtained.

Workup

  1. extractionthe residue is extracted from ethyl acetate
  2. washThe combined organic phases are washed with dilute HCl solution and saturated NaCl solution
  3. filtrationfiltered through a Whatman
  4. filtrationfilter
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1a727ba01de04ffa957a0a1c21630526
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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