Benzylamine → Benzyl Isothiocyanate

HRID 1166038Notes

Reaction equation

HRID 1166038 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(Cl)=[S:17]>C(OCC)(=O)C>[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[C:16]=[S:17]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 10040Thiophosgene

Product 1

HCID 2346Benzyl Isothiocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Benzylamine (1.5 g) and triethyl amine (2.9 g) were dissolved in anhydrous ethyl acetate (50 ml) and stirred under ice cooling. Thiophosgene (4.9 g) dissolved in ethyl acetate (50 ml) was slowly added to the stirred solution. The solution was heated at reflux for 2 hr and filtered. Evaporation of the solvent afforded (isothiocyanatomethyl)-benzene which was used in the next step without purification. 1H NMR, CDCl3, 4.72 (2H, s), 7.30-7.40 (5H, m).

Workup

  1. additionwas slowly added to the stirred solution
  2. temperatureThe solution was heated
  3. temperatureat reflux for 2 hr
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-53a7d2a350474250ac1c8894c645fa88
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

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