Sodium Hydroxide → 3-Amino-2,2,4,4-tetramethylthietan-1,1-dioxide

HRID 462847Notes

Reaction equation

HRID 462847 reaction equation
[NH2:1][CH:2]1[C:5]([CH3:7])([CH3:6])[S:4][C:3]1([CH3:9])[CH3:8].[O-:10]I(=O)(=O)=O.[Na+].[OH-:16].[Na+]>O>[NH2:1][CH:2]1[C:5]([CH3:7])([CH3:6])[S:4](=[O:10])(=[O:16])[C:3]1([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 115210993-Amino-2,2,4,4-tetramethylthietaneHCID 23667635Sodium periodate

Product 1

HCID 137335683-Amino-2,2,4,4-tetramethylthietan-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 14.53 g. (0.1 mole) 3-amino-2,2,4,4-tetramethylthietane and 64.17 g. (0.3 mole) sodium m-periodate in 500 ml. water was stirred overnight at room temperature. The reaction mixture was adjusted to pH 13 with sodium hydroxide solution and the precipitated sodium iodate removed by filtration. The filtrate was washed with 100 ml. ethyl ether, the aqueous phase extracted continuously with methylene chloride over 18 hours, the extract dried (MgSO4) and solvent evaporated in vacuo. The residual solid was recrystallized from ethyl acetate to provide 8.5 g. of product, M.P. 104°-106.5° C. A second crop of crystals was obtained, 2.7 g., M.P. 103°-106° C. Total yield, 63%.

Workup

  1. customthe precipitated sodium iodate removed by filtration
  2. washThe filtrate was washed with 100 ml
  3. extractionethyl ether, the aqueous phase extracted continuously with methylene chloride over 18 hours
  4. dry with materialthe extract dried (MgSO4) and solvent
  5. customevaporated in vacuo
  6. customThe residual solid was recrystallized from ethyl acetate
  7. customto provide 8.5 g
  8. customA second crop of crystals was obtained

Sources & evidence

ORD record
ord-0df5d422add44068b5682657cd957983
Source dataset
uspto-grants-1985_05
Patent number
US04517379

Reaction notes

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