Ethanethiol → HCID 12726338, compound

HRID 1758257Notes

Reaction equation

HRID 1758257 reaction equation
[Na].[CH2:2]([SH:4])[CH3:3].[CH2:5]([O:7][CH:8]([O:11][CH2:12][CH3:13])[CH2:9]Br)[CH3:6]>C(O)C>[CH2:5]([O:7][CH:8]([O:11][CH2:12][CH3:13])[CH2:9][S:4][CH2:2][CH3:3])[CH3:6]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 5360545Sodium

Product 1

HCID 12726338HCID 12726338, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (10.7 g, 0.463 mole) was dissolved in ethanol (500 ml) and ice cooled. Ethanethiol (34.4 ml, 0.463 mole) was added, followed after 15 mins. by bromoacetaldehyde diethylacetal (83.8 g, 0.421 mole). The mixture was refluxed 3 hours and the volume reduced to 200 ml by distillation of some of the ethanol at atmospheric pressure. Ether (500 ml) was added and the solution washed with water (3×200 ml), dried over MgSO4 and evaporated at atmospheric pressure. The residue was distilled to provide title compound (70.46 g, 99%) bp 96°-100° C./20 mm Hg.

Workup

  1. temperatureice cooled
  2. temperatureThe mixture was refluxed 3 hours
  3. distillationthe volume reduced to 200 ml by distillation of some of the ethanol at atmospheric pressure
  4. additionEther (500 ml) was added
  5. washthe solution washed with water (3×200 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated at atmospheric pressure
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-bfff9181008147e7b005e8ac04fdac3a
Source dataset
uspto-grants-1983_02
Patent number
US04372962

Reaction notes

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