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With triethylamine In N,N-dimethyl-formamide for 3h; Cooling with ice; |
5 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N',N' dimethylsulfamide (Compound #6)
EXAMPLE 5 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N',N' dimethylsulfamide (Compound #6) Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Elemental Analysis: Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90 1H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m, 1H, NH), 4.35 (m, 1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5
EXAMPLE 5; N-(2,3-Dihvdro-benzori,41dioxin-2-vlmethvl)-N',N' dimethylsulfamide(Compound No.6); Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 ml_) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSC>4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane -1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid.mp 76 - 78°CMS 273 (MH+)Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.901H NMR (CDCI3) 5 6.87 (m, 4H), 4.59 (bd m, 1H, NH), 4.35 (m, 1H), 4.27 (dd, J = 2.3, 11.4 Hz, 1H), 4.04 (dd, J = 7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; Cooling with ice bath; |
5 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N',N' dimethylsulfamide (Compound #6)
Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Elemental Analysis: Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90 1H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m, 1 H, NH), 4.35 (m, 1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1 H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5
Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Elemental Analysis: Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90 1H NMR (CDCl3) δ6.87 (m, 4H), 4.59 (bd m, 1H, NH), 4.35 (m, 1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5
Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Elemental Analysis: Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90 1H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m, 1 H, NH), 4.35 (m, 1 H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5
Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Elemental Analysis: Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90 1H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m, 1H, NH), 4.35 (m, 1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N',N'dimethylsulfamide (Compound #6)
Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Elemental Analysis: Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78. Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90. 1H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m, 1H, NH), 4.35 (m,1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5
Racemic 2,3-dihydro-1 ,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 ml_) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO-O and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl ,acetate:Heptane - 1 :1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76 - 78°CMS 273 (MH+) Elemental Analysis:Anal CaIc: C, 48.52; H, 5.92; N, 10.29; S5 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.901H NMR (CDCI3) 56.87 (m, 4H), 4.59 (bd m, 1 H, NH), 4.35 (m, 1 H)1 4.27 (dd, J = 2.3, 11.4 Hz, 1 H), 4.04 (dd, J = 7.0, 11.4, 1 H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5
Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid.mp 76-78° C.MS 273 (MH+)Elemental Analysis:Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.901H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m,1H, NH), 4.35 (m,1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; |
5 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N',N' dimethylsulfamide
EXAMPLE 5 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-N',N' dimethylsulfamide (Compound #6) Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane-1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid. mp 76-78° C. MS 273 (MH+) Anal Calc: C, 48.52; H, 5.92; N, 10.29; S, 11.78 Anal Found: C, 48.63; H, 5.62; N, 10.20; S, 11.90 1H NMR (CDCl3) δ 6.87 (m, 4H), 4.59 (bd m, 1H, NH), 4.35 (m, 1H), 4.27 (dd, J=2.3, 11.4 Hz, 1H), 4.04 (dd, J=7.0, 11.4, 1H), 3.36 (m, 2H), 2.82 (s, 6H). |
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With triethylamine In N,N-dimethyl-formamide for 3h; |
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