2-isothiocyanatopropan-2-ylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Anhydrous hydrazine (1.161 mL, 37.0 mmol) (Sigma-Aldrich) was added to a stirring solution of (2-isothiocyanatopropan-2-yl)benzene (6.56 g, 37.0 mmol) in EtOH (150 mL). The reaction was stirred at RT for 2 h to give N-(2-phenylpropan-2-yl)hydrazinecarbothioamide. MS (ESI, pos. ion) m/z: 210.2 (M+1). The material was used without purification.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Anhydrous hydrazine (1.161 mL, 37.0 mmol) (Sigma-Aldrich) was added to a stirring solution of (2-isothiocyanatopropan-2-yl)benzene (6.56 g, 37.0 mmol) in EtOH (150 mL). The reaction was stirred at RT for 2 h to give N-(2-phenylpropan-2-yl)hydrazinecarbothioamide. MS (ESI, pos. ion) m/z: 210.2 (M+1). The material was used without purification.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cumylamine (5.32 mL, 37.0 mmol) (TCI America) and Et3N (16.97 mL, 122 mmol) (Aldrich) were mixed in THF (40 mL) at 0° C. under a nitrogen atmosphere. Carbon disulfide (2.224 mL, 37.0 mmol) (J.T.Baker) was added dropwise via syringe over the course of 10 min. The reaction was stirred at 0° C. for 1 h before being warmed to RT and stirred for 1 h. p-Toluenesulfonyl chloride (7.76 g, 40.7 mmol) (Fluka) was added, and the reaction was stirred at RT for 1 h. The mixture was quenched with 1 M HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated to give (2-isothiocyanatopropan-2-yl)benzene. before being warmed to RT was added the reaction was stirred at RT for 1 h The mixture was quenched with 1 M HCl extracted with EtOAc The organic layer was washed with brine dried over MgSO4 concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Anhydrous hydrazine (1.161 mL, 37.0 mmol) (Sigma-Aldrich) was added to a stirring solution of (2-isothiocyanatopropan-2-yl)benzene (6.56 g, 37.0 mmol) in EtOH (150 mL). The reaction was stirred at RT for 2 h to give N-(2-phenylpropan-2-yl)hydrazinecarbothioamide. MS (ESI, pos. ion) m/z: 210.2 (M+1). The material was used without purification.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cumylamine (5.32 mL, 37.0 mmol) (TCI America) and Et3N (16.97 mL, 122 mmol) (Aldrich) were mixed in THF (40 mL) at 0° C. under a nitrogen atmosphere. Carbon disulfide (2.224 mL, 37.0 mmol) (J.T.Baker) was added dropwise via syringe over the course of 10 min. The reaction was stirred at 0° C. for 1 h before being warmed to RT and stirred for 1 h. p-Toluenesulfonyl chloride (7.76 g, 40.7 mmol) (Fluka) was added, and the reaction was stirred at RT for 1 h. The mixture was quenched with 1 M HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated to give (2-isothiocyanatopropan-2-yl)benzene. before being warmed to RT was added the reaction was stirred at RT for 1 h The mixture was quenched with 1 M HCl extracted with EtOAc The organic layer was washed with brine dried over MgSO4 concentrated