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

HRID 2272991Notes

Reaction equation

HRID 2272991 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) is added trifluoroacetic acid (20 mL) slowly at 0° C. under a nitrogen atmosphere. The reaction mixture is stirred for 30 minutes followed slowly by water (60 mL). The reaction is left at 0° C. for 15 minutes. The solid precipitated is filtered and washed several times with water until the pH of the filtrate was neutral. The white solid (1.4 g, 98%) is dried in the Buchner funnel and used immediately for the next reaction; 1H NMR (400 MHz, DMSO-d6): δ6.73 (s, 2H), 2.48 (s, 6H), 2.15 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-671f8020009646f4a0e44fd04cd22e90
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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