Triethylamine → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

HRID 1895886Notes

Reaction equation

HRID 1895886 reaction equation
[OH:1][N:2]=C(OCC)C.C(N(CC)CC)C.[C:15]1([CH3:27])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23](Cl)(=[O:25])=[O:24].Cl(O)(=O)(=O)=O>CN(C=O)C.O>[C:15]1([CH3:27])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23]([O:1][NH2:2])(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 24247Perchloric AcidHCID 99894Ethyl acetohydroximate

Product 1

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of ethyl N-hydroxyacetimidate (4.72 g, 45.7 mmol) in DMF (453 ml) was added triethylamine (9.53 ml, 68.6 mmol) followed by portionwise addition of mesitylenesulfonyl chloride (1, 10 g, 45.7 mmol). The reaction mixture was stirred for 2 hours at room temperature then poured into ice water (150 mL). The resulting precipitate was collected by vacuum filtration. The collected solids were treated with neat perchloric acid (32.8 ml, 229 mmol) and stirred until homogeneous. Distilled water (30 mL) was used to titurate white crystals of O-mesitylenesulfonylhydroxylamine (2, 8.31 g, 38.6 mmol, 84% yield). MS APCI: [M+H]+ m/z 216.3.

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. stirringstirred until homogeneous

Sources & evidence

ORD record
ord-3cfe3743c7414741b0edd214e4259b4d
Source dataset
uspto-grants-2013_08
Patent number
US08518911B2

Reaction notes

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