Diethyl Ether → HCID 21936578, compound

HRID 1241613Notes

Reaction equation

HRID 1241613 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:6]#[N:7])[CH3:2].[H-].[Na+].[C:14]([N:19]=[C:20]=[S:21])([CH2:17][CH3:18])([CH3:16])[CH3:15].C(OCC)C>CN(C=O)C.Cl.O>[CH2:1]([C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:10]=1[NH:11][C:20]([NH:19][C:14]([CH3:16])([CH3:15])[CH2:17][CH3:18])=[S:21])[CH3:2]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 27353304-Amino-3-ethylbenzonitrileHCID 11105389Neopentyl isothiocyanate

Product 1

HCID 21936578HCID 21936578, compoundYield 56.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 3-ethyl-4-aminobenzonitrile (1.35 g, 9.29 mmol) in DMF (10 mL) at room temperature was added sodium hydride (0.28 g, 80%, 9.29 mmol). The mixture was heated to 70° C. for 40 minutes and was then cooled to room temperature. A solution of tert-amyl isothiocyanate (1.0 g, 7.74 mmol) in DMF (1 mL) was added by syringe and the reaction was stirred at 70° C. overnight. The cooled reaction mixture was diluted with 2N HCl and water and the mixture was extracted with ethyl acetate. The organic phase was dried and concentrated to afford an oil. The crude product was taken up in a minimal amount of diethyl ether and the solution was made turbid by adding petroleum ether. Sonication resulted in the formation of a precipitate which was collected by filtration to afford 1.2 g (56%) of 1-(2-ethyl-4-cyanophenyl)-3-(1,1-dimethyl-propyl)-thiourea as an off-white solid which was used without further purification.

Workup

  1. temperaturewas then cooled to room temperature
  2. customThe cooled reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customto afford an oil
  7. customSonication
  8. customresulted in the formation of a precipitate which
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7ef2ff28e2dd4c50bd159f137cf3edee
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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