Benzoyl isothiocyanate → HCID 86697920, compound

HRID 470231Notes

Reaction equation

HRID 470231 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-58756997419040de91754409207fa5bf
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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