Trifluoroacetic acid → 2-Amino-2-(4-chlorophenyl)ethanesulfonamide

HRID 423092Notes

Reaction equation

HRID 423092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:14]C(=O)OC(C)(C)C)[CH2:9][S:10](=[O:13])(=[O:12])[NH2:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:14][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:9][S:10]([NH2:11])(=[O:12])=[O:13]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57750308Tert-butyl 1-(4-chlorophenyl)-2-sulfamoylethylcarbamate2×

Product 1

HCID 577503602-Amino-2-(4-chlorophenyl)ethanesulfonamideYield 97.1%

Procedure

Tert-butyl 1-(4-chlorophenyl)-2-sulfamoylethylcarbamate (Intermediate 79) (325 mg, 0.97 mmol) was treated with trifluoroacetic acid (8 mL). The resulting solution was stirred for 15 minutes at room temperature. The mixture was concentrated under reduced pressure and the residue was purified by ion exchange chromatography, using an SCX column. The column was washed with methanol and the desired product was eluted using ammonia in methanol (2M) and pure fractions were evaporated to dryness to afford 2-amino-2-(4-chlorophenyl)ethanesulfonamide (221 mg, 97%) as a near colourless solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by ion exchange chromatography
  3. washThe column was washed with methanol
  4. washthe desired product was eluted
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-c9bb3b2977934a038654faf21ae6b2ad
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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