Trifluoroacetic acid → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

HRID 570598Notes

Reaction equation

HRID 570598 reaction equation
C(OC([NH:8][O:9][S:10]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])(=[O:12])=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>O>[O:9]([S:10]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])(=[O:11])=[O:12])[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

Product 1

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solid product N-(tert.-butoxycarbonyl)-O-(mesitylsulfonyl)-hydroxylamine (2.1 g, 6.6 mmol) was added trifluoroacetic acid (20 mL) slowly at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes followed slowly by water (60 mL). The reaction was left at 0° C. for 15 minutes. The solid precipitated was filtered and washed several times with water until the pH of the filtrate was neutral. The white solid (1.4 g, 98%) was dried in the Buchner funnel and used immediately for the next reaction; 1H NMR (400 MHz, DMSO-d6): δ 6.73 (s, 2H), 2.48 (s, 6H), 2.15 (s, 3H).

Workup

  1. waitThe reaction was left at 0° C. for 15 minutes
  2. customThe solid precipitated
  3. filtrationwas filtered
  4. washwashed several times with water until the pH of the filtrate
  5. dry with materialThe white solid (1.4 g, 98%) was dried in the Buchner funnel
  6. customused immediately for the next reaction

Sources & evidence

ORD record
ord-506de3fb322d431c8c9d8b1147ffda07
Source dataset
uspto-grants-2015_05
Patent number
US09023851B2

Reaction notes

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