Propane sultone → HCID 21535946, compound

HRID 1077081Notes

Reaction equation

HRID 1077081 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].C1[CH2:11][S:8](=[O:10])(=[O:9])[O:7]C1>CO>[SH:3][CH2:1][CH2:2][CH2:11][S:8]([O-:10])(=[O:9])=[O:7].[NH4+:4]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 2723949Thioacetamide

Product 1

HCID 21535946HCID 21535946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.0 grams of thioacetamide and 81.5 grams of 1,3-propane sultone in 700 ml of methanol is refluxed at atmospheric pressure for 10 minutes. The reaction mixture is then concentrated by evaporation of solvent to 200 ml, and 600 ml of anhydrous diethyl ether is added. A white precipitate is formed, is collected by filtration and then is dissolved in 350 ml of ethanol. After drying and decolorizing with 4A molecular sieves* and charcoal, addition of anhydrous diethyl ether to the filtered solution, and refiltration, the yield is 59.7 g (50% of theoretical) of shiny white crystals of ammonium 3-mercaptopropanesulfonate having a melting point of 160°C. C3H11NO3S2Calculated % C, 20.8; H, 6.4; N, 8.1

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation of solvent to 200 ml, and 600 ml of anhydrous diethyl ether
  2. additionis added
  3. customA white precipitate is formed
  4. filtrationis collected by filtration
  5. dissolutionis dissolved in 350 ml of ethanol
  6. customAfter drying
  7. additiondecolorizing with 4A molecular sieves* and charcoal, addition of anhydrous diethyl ether to the filtered solution, and refiltration

Sources & evidence

ORD record
ord-06ada80470f54fda97d07d9102d8e4bf
Source dataset
uspto-grants-1976_05
Patent number
US03959362

Reaction notes

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