Benzylamine → Benzyl Isothiocyanate

HRID 584556Notes

Reaction equation

HRID 584556 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-d2e5574eb5ac4e7191fa83a2a3052b26
Source dataset
uspto-grants-2005_08
Patent number
US06927193B2

Reaction notes

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