Acetyl isothiocyanate → N-[5-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-thiazolidin-2-ylidene]-acetamide

HRID 1260344Notes

Reaction equation

HRID 1260344 reaction equation
[CH2:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]2[O:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[O:12][C:7]=2[CH:6]=1)[C:2]#[CH:3].[C:19]([N:22]=[C:23]=[S:24])(=[O:21])[CH3:20]>C1COCC1>[CH2:3]=[C:2]1[S:24][C:23](=[N:22][C:19](=[O:21])[CH3:20])[N:4]([C:5]2[CH:18]=[CH:17][C:8]3[O:9][C:10]([F:15])([F:16])[C:11]([F:14])([F:13])[O:12][C:7]=3[CH:6]=2)[CH2:1]1

Participants

4

Reactant 2

HCID 128851Acetyl isothiocyanateHCID 86619165Prop-2-ynyl-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine

Product 1

HCID 86619166N-[5-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-thiazolidin-2-ylidene]-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An alternative procedure to prepare the titled compound follows. The propargylaniline (Example 22A, 31.08 g, ˜119 mmol) was dissolved into THF (300 mL) and treated with acetylisothiocyanate (11.5 mL, 131 mmol). After being stirred at room temperature briefly, it was heated to approximately 55° C. overnight, and at 60-65° C. for another 6 days. Then the mixture was concentrated and reconcentrated from CH2Cl2/hexanes to give a semi-solid which was mixed into 3:1 Et2O/hexanes and chromatographed on neutral alumina (40% Et2O/hexanes then 40% Et2O/CH2Cl2) to give the titled compound.

Workup

  1. temperatureit was heated to approximately 55° C. overnight
  2. concentrationThen the mixture was concentrated
  3. customto give a semi-solid which
  4. customchromatographed on neutral alumina (40% Et2O/hexanes

Sources & evidence

ORD record
ord-e6b09cd5d83c403094f9afdd432360d1
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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