2-Propanethiol → ethyl (isopropylthio)acetate

HRID 1722672Notes

Reaction equation

HRID 1722672 reaction equation
[Na].[SH:2][CH:3]([CH3:5])[CH3:4].Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C>[CH3:4][CH:3]([S:2][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:5]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 7748Ethyl bromoacetateHCID 5360545Sodium

Product 1

HCID 10773300ethyl (isopropylthio)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To sodium (4.2 g, 0.18 mol) in ethanol (100 mL) was added 2mercaptopropane (20 mL), 0.21 mol) followed by ethyl bromoacetate (10 mL, 0.090 mol). The mixture was stirred for 12 hours, concentrated, partitioned between ether and water and washed with water. The organic phase was dried over MgSO4, evaporated and distilled to afford the desired product. B.P. 58°-62° C. (1 mm).

Workup

  1. concentrationconcentrated
  2. custompartitioned between ether and water
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. distillationdistilled

Sources & evidence

ORD record
ord-621540d05d9e4f92bffb5ed2715a18aa
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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