Benzoyl isothiocyanate → HCID 86697930, compound

HRID 338108Notes

Reaction equation

HRID 338108 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]12[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH:10]1[CH2:9][O:8][NH:7]2.[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[C:21]([NH:29][C:30]([N:7]1[C:6]2([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH:10]2[CH2:9][O:8]1)=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86714334HCID 86714334, compound

Product 1

HCID 86697930HCID 86697930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 6a-(2-thienyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (7.16 g, 24.2 mmol) in THF (161 mL) is added benzoyl isothiocyanate (3.94 g, 24.2 mmol). The reaction is stirred for 1 hour at room temperature, concentrated under reduced pressure, and triturated with hexane/ethyl acetate (1:1) to give the title compound. ES/MS (m/e): 459 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customtriturated with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-dcb3dd8a8a4f405b9647439d4f999735
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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