Benzylamine → Benzyl Isothiocyanate

HRID 1248932Notes

Reaction equation

HRID 1248932 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]>O1CCCC1>[CH2:1]([N:8]=[C:16]=[S:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 10040Thiophosgene

Product 1

HCID 2346Benzyl Isothiocyanate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of benzylamine (5.4 g, 0.05 mole) and triethylamine (15.4 ml, 0.11 mole) in 50 ml of tetrahydrofuran was added dropwise to a solution of thiophosgene (4.2 ml, 0.055 mole) in 50 ml of tetrahydrofuran with cooling to -10° C. over a period of twenty minutes. The mixture was stirred at 25° C. for 2.75 hours and filtered. The filtrate was treated with charcoal, then filtered and evaporated to an oil. The oil was diluted with hexane:ethyl acetate (90:10) and purified on a flash silica column using hexane:ethyl acetate (90:10) as the eluant to yield benzyl isothiocyanate as a yellow oil.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was treated with charcoal
  3. filtrationfiltered
  4. customevaporated to an oil
  5. additionThe oil was diluted with hexane:ethyl acetate (90:10)
  6. custompurified on a flash silica column

Sources & evidence

ORD record
ord-e78d05ee57f348f997756c0366735920
Source dataset
uspto-grants-1986_12
Patent number
US04628059

Reaction notes

Loading…