Benzene → n-Heptyl-diethyl-thiourea

HRID 224630

Reaction equation

HRID 224630 reaction equation
[CH2:1]([N:8]=[C:9]=[S:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:11]([NH:13]CC)[CH3:12].[CH:16]1C=CC=C[CH:17]=1>>[CH2:1]([N:8]([CH2:16][CH3:17])[C:9]([NH:13][CH2:11][CH3:12])=[S:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 241BenzeneHCID 8021DiethylamineHCID 78152Heptane, 1-isothiocyanato-

Product 1

HCID 20555250n-Heptyl-diethyl-thiourea

Procedure

To a solution of 3.14 grams (0.02 mole) of heptyl isothiocyanate dissolved in 15 milliliters of benzene was added 1.46 grams (0.02 mole) of diethylamine. The temperature rose to about 50° C. The mixture was refluxed on a steam bath for 20 minutes until a neutral pH was obtained. The mixture was then evaporated under vacuum to give 4.8 grams of n-heptyl-diethyl-thiourea. To this product, 4.1 grams (0.02 mole) of bromoethylamine hydrobromide and 25 milliliters of ethanol 2B was added. The mixture was refluxed on a steam bath for four hours and then permitted to stand overnight at ambient temperature. The mixture was then refluxed an additional three hours. The mixture was evaporated under vacuum to yield 8.83 grams of a yellow gel-like liquid, ND30 =1.5410. The structure of the product was confirmed by NMR.

Workup

  1. customrose to about 50° C
  2. temperatureThe mixture was refluxed on a steam bath for 20 minutes until a neutral pH
  3. customwas obtained
  4. customThe mixture was then evaporated under vacuum

Sources & evidence

ORD record
ord-6eeeb19703db41dd8f6ffd9972ba5eb5
Source dataset
uspto-grants-1980_11
Patent number
US04233318

Linked notes

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