Diethyl Sulfate → Eptam

HRID 1606416Notes

Reaction equation

HRID 1606416 reaction equation
[CH2:1]([N:4]([CH2:10][CH2:11][CH3:12])[C:5](=[S:9])[O:6]CC)[CH2:2][CH3:3].S(OCC)(O[CH2:17][CH3:18])(=O)=O>CO>[CH2:10]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:9])[S:6][CH2:17][CH3:18])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 6163Diethyl SulfateHCID 15793180Carbamic acid, dipropylthio-, O-ethyl ester

Product 1

HCID 12968EptamYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

94.5 g. (0.5 moles) of O-ethyl N,N-dipropyl-thiocarbamate are introduced into a 250 ml. round-bottomed flask, and 4.7 g. of diethyl sulfate are added. The mixture is refluxed for 80 minutes on an oil bath heated to 160°C. The progress of the reaction is monitored by sampling the reaction mixture and recording the UV spectra of the samples in methanol. The absorption maximum at 250 nm, characteristic of the =S group of the starting substance, gradually decreases, and disappears when the isomerization is completed. Then the reaction mixture is cooled, and the small amount of oily substance separated at the bottom of the flask is removed. The upper phase is distilled in vacuo. The title compound boils at 122°-124°C/19 Hgmm. 86.0 g. (91 %) of S-ethyl N,N-di-propyl-thiocarbamate are obtained; nD 30 = 1.4750.

Workup

  1. temperatureThe mixture is refluxed for 80 minutes on an oil bath
  2. aliquotby sampling the reaction mixture
  3. temperatureThen the reaction mixture is cooled
  4. customthe small amount of oily substance separated at the bottom of the flask
  5. customis removed
  6. distillationThe upper phase is distilled in vacuo

Sources & evidence

ORD record
ord-5ffc3040fcea4f38a4ad667ff1a95f21
Source dataset
uspto-grants-1976_04
Patent number
US03953427

Reaction notes

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