Trifluoroacetic acid → 2-Methoxy-4-nitrobenzenesulfonamide

HRID 970433Notes

Reaction equation

HRID 970433 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[O:18][CH3:19])(=[O:8])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(OCC)(=O)C>[CH3:19][O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[S:6]([NH2:5])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 47190031N-tert-Butyl-2-methoxy-4-nitro-benzenesulfonamide

Product 1

HCID 203309102-Methoxy-4-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.1 g (28.1 mmol) of N-tert-butyl-2-methoxy-4-nitro-benzenesulfonamide is mixed with 350 ml of trifluoroacetic acid and stirred for 20 hours at room temperature. The trifluoroacetic acid is drawn off, and the remaining residue is then digested with ethyl acetate. 5.0 g (21.6 mmol, corresponding to 77% of theory) of the product is obtained. The ethyl acetate phase is concentrated by evaporation, and the residue that is obtained is purified by chromatography (DCM/EtOH 95:5, Flashmaster II). Another 0.84 g (3.6 mmol, corresponding to 13% of theory) of the product is obtained.

Workup

  1. custom5.0 g (21.6 mmol, corresponding to 77% of theory) of the product is obtained
  2. concentrationThe ethyl acetate phase is concentrated by evaporation
  3. customthe residue that is obtained
  4. customis purified by chromatography (DCM/EtOH 95:5, Flashmaster II)
  5. customAnother 0.84 g (3.6 mmol, corresponding to 13% of theory) of the product is obtained

Sources & evidence

ORD record
ord-2fd1b7f0f0be4c039eb33a8ec79181f0
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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