Diethyl Ether → 3-(3,5-Difluorophenyl)propyl Isothiocyanate

HRID 1193601Notes

Reaction equation

HRID 1193601 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH2:12])[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.[C:20](Cl)(Cl)=[S:21].C(OCC)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]=[C:20]=[S:21])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 140499133-(3,5-Difluorophenyl)propan-1-amine

Product 1

HCID 140499143-(3,5-Difluorophenyl)propyl IsothiocyanateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(3,5-difluorophenyl)propylamine (0.0327 mol) and triethylamine (0.072 mol) in tetrahydrofuran (20 ml) was added dropwise to a solution of thiophosgene (0.0392 mol) in tetrahydrofuran at 0°. The reaction was stirred 2 hours at room temperature then ethyl ether was added and the mixture filtered. The filtrate was concentrated and distilled (Kugelrohr) to yield 3.8 g (55%) of a yellow oil.

Workup

  1. filtrationthe mixture filtered
  2. concentrationThe filtrate was concentrated
  3. distillationdistilled (Kugelrohr)

Sources & evidence

ORD record
ord-2b91444dcacf44ffb40a8e8ff61acae6
Source dataset
uspto-grants-1989_03
Patent number
US04810811

Reaction notes

Loading…