Triethylamine → 3,5-Difluorobenzyl isothiocyanate

HRID 1248936Notes

Reaction equation

HRID 1248936 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6].C(N(CC)CC)C.[C:18](Cl)(Cl)=[S:19]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][N:6]=[C:18]=[S:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 1452113,5-Difluorobenzylamine

Product 1

HCID 201291633,5-Difluorobenzyl isothiocyanateYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 3,5-difluorobenzylamine (6.5 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 then filtered. The filtrate was treated with charcoal, 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 8.0 g (62%) of 3,5-difluorobenzyl 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
  7. washeluted with hexane:ethyl acetate (90:10)

Sources & evidence

ORD record
ord-ed3f1007dea7450ebf52cba1892f0e5b
Source dataset
uspto-grants-1986_12
Patent number
US04628059

Reaction notes

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