methanesulfonyl fluoride

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

Procedure: Chem. Abstracts 56:7116f, abstracting Sokolsku et al., Izvest. Akad Nauk S.S.S.R., Otdel Khem Nauk 1606 (1968), describes the reaction of CH3SO2F with (C2H5)2NH after one day to give 96.5% CH3SO2N(C2H5)2.

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

Procedure: Chem. Abstracts 56:7116f, abstracting Sokolsku et al., Izvest. Akad Nauk S.S.S.R., Otdel Khem Nauk 1606 (1968), describes the reaction of CH3SO2F with (C2H5)2NH after one day to give 96.5% CH3SO2N(C2H5)2.

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

Procedure: To a stirred solution of 1.0 M tetrabutylamonium fluoride (0.45 mL, 0.45 mmol) in 2.0 mL of THF in the presence of molecular sieves (4 Å, 1.0 g) was added a mixture of methylsufonyl fluoride (21 μL, 0.30 mmol) and trans-1,2,3,5,6,10b-Hexahydro-6-[4'-(3-hydroxy-1(Z)-propenyl)phenyl]pyrrolo[2,1-a]isoquinoline (18) (23 mg, 0.075 mmol) in 5 mL of THF at room temperature. The reaction mixture was heated at reflux for 16 h, cooled to room temperature, filtered through a sintered glass funnel with aid of a small amount of methylene chloride (10 mL) and ethyl acetate (10 mL). The filtrate was concentrated to afford a crude product. Flash chromatography with 2.3% MeOH, 0.046% Et3N in methylene chloride gave 10 mg of thick colorless oil (43% yield). 1H NMR (CDCl3) δ 1.73-2.05 (m, 3H, C2H2 & C1H), 2.30-2.2.44 (m, 1H, C1H), 2.579 (dt, 1H, J=9.0, 8.7 Hz, C3H), 2.869 (dd, 1H, J=5.1, 11.1 Hz, C5H), 2.90-3.03 (m, 2H, C3H & C5H), 3.480 (dd, 1H, J=7.2, 9.0 Hz, C10bH), 4.125 (t, 1H, J=4.8 Hz, C6H), 6.865 (d, 1H, J=7.5 Hz, aryl), 6.995 (d, 2H, J=8.1 Hz, C6 phenyl aryl), 7.04-7.20 (m, 3H, aryl), 7.575 (d, 2H, J=8.1 Hz, C6 phenyl aryl) (aromatic), 126.30, 129.30, 130.97, 137.23. The reaction mixture was heated at reflux for 16 h filtered through a sintered glass funnel with aid of a small amount of methylene chloride (10 mL) and ethyl acetate (10 mL) The filtrate was concentrated to afford a crude product

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

Procedure: A mixture of 1.0 g. of ethyl 4-[3-(p-chlorophenyl)propylamino]benzoate, 20 ml. of dry dichloromethane and 2.5 ml. of methane sulfonyl fluoride is stirred for 18 hours, then refluxed for 3 hours. The solution is poured into 30 ml. of water and adjusted to pH 10 with 10N sodium hydroxide. The dichloromethane layer is separated and saved. The aqueous layer is extracted with two 20 ml. portions of dichloromethane. The organic layers are combined, washed with 10 ml. of water, dried over anhydrous magnesium sulfate, and evaporated to yield 1.80 g. of the desired product as a light yellow oil. A mixture of 1.0 g refluxed for 3 hours The solution is poured into 30 ml The dichloromethane layer is separated The aqueous layer is extracted with two 20 ml washed with 10 ml of water, dried over anhydrous magnesium sulfate evaporated to yield 1.80 g

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

Procedure: Chem. Abstracts 56:7116f, abstracting Sokolsku et al., Izvest. Akad Nauk S.S.S.R., Otdel Khem Nauk 1606 (1968), describes the reaction of CH3SO2F with (C2H5)2NH after one day to give 96.5% CH3SO2N(C2H5)2.