Triethylamine → 3-Fluorobenzyl isothiocyanate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].C(N(CC)CC)C.[C:17](Cl)(Cl)=[S:18]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:6]=[C:17]=[S:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution of 3-fluorobenzylamine (6.3 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 eluted with hexane:ethyl acetate (90:10) to yield 4.3 g (51%) of 3-fluorobenzyl isothiocyanate as a yellow oil.
Workup
- filtrationfiltered
- additionThe filtrate was treated with charcoal
- filtrationfiltered
- customevaporated to an oil
- additionThe oil was diluted with hexane:ethyl acetate (90:10)
- custompurified on a flash silica column
- washeluted with hexane:ethyl acetate (90:10)
Sources & evidence
- ORD record
- ord-54a2c470bbc24b58b016c197a1aad4d7
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628059
Reaction notes
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