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

HRID 1262976Notes

Reaction equation

HRID 1262976 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-541f6130e36b430d9caca9959ec00a1c
Source dataset
uspto-grants-1984_06
Patent number
US04454328

Reaction notes

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