Diethyl Sulfate → Butylate

HRID 1606418

Reaction equation

[CH2:1]([N:5]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6](=[S:10])[O:7]CC)[CH:2]([CH3:4])[CH3:3].S(OCC)(O[CH2:19][CH3:20])(=O)=O>>[CH2:11]([N:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[C:6](=[O:10])[S:7][CH2:19][CH3:20])[CH:12]([CH3:13])[CH3:14]

Participants

Reactant 2

HCID 6163Diethyl Sulfate

HCID 21542997O-ethyl N,N-diisobutyl-thiocarbamate

Product 1

HCID 16181ButylateYield 92%

Conditions

Temperature: 160 °C

Procedure

43.4 g. (0.2 mole) of O-ethyl N,N-diisobutyl-thiocarbamate are introduced into a 100 ml. round-bottomed flask, and 2.5 g. of diethyl sulfate are added. The mixture is refluxed for 90 minutes on an oil bath heated to 160°C, and thereafter the product is isolated by vacuum distillation. 39.8 g. (92 %) of S-ethyl N,N-diisobutyl-thiocarbamate are obtained; b.p.: 137°-138°C/20 Hgmm., nD25 = 1.4689.

Workup

temperatureThe mixture is refluxed for 90 minutes on an oil bath
customthe product is isolated by vacuum distillation

Sources & evidence

ORD record: ord-cd703b39e32d40d6a0aad0997c8a403a
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03953427

Linked notes

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