Benzoyl isothiocyanate → HCID 86697920, compound

HRID 338105Notes

Reaction equation

HRID 338105 reaction equation
[CH2:1]([N:4]1[CH2:11][CH:10]2[C:6]([C:12]3[S:13][C:14]([F:17])=[CH:15][CH:16]=3)([NH:7][O:8][CH2:9]2)[CH2:5]1)[CH:2]=[CH2:3].[C:18]([N:26]=[C:27]=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[CH2:1]([N:4]1[CH2:11][CH:10]2[C:6]([C:12]3[S:13][C:14]([F:17])=[CH:15][CH:16]=3)([N:7]([C:27]([NH:26][C:18](=[O:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[S:28])[O:8][CH2:9]2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86697921HCID 86697921, compound

Product 1

HCID 86697920HCID 86697920, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-allyl-6a-(5-fluoro-2-thienyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (4.22 g, 16.59 mmol) in tetrahydrofuran (83 mL) is added benzoyl isothiocyanate (2.7 mL, 19.9 mmol). The resulting solution is stirred under nitrogen at room temperature for 19 hours. The solution is concentrated and the residue is purified by silica gel flash chromatography eluting with hexanes/ethyl acetate (two-step gradient from 80:20 to 70:30 to 60:40) to give the title compound (6.92 g, 100%). ES/MS (m/e): 418 (M+H).

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue is purified by silica gel flash chromatography
  3. washeluting with hexanes/ethyl acetate (two-step gradient from 80:20 to 70:30 to 60:40)

Sources & evidence

ORD record
ord-4dba3b2cde56495d87efc3c75b34173a
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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