Novel preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole
A sulfonyl and tri-substituted technology, applied in the field of organic synthesis, can solve the problems such as no public report on the preparation technology, and achieve the effects of high reaction efficiency and mild reaction conditions
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Embodiment 1
[0021] Example 1: Preparation of 5-benzenesulfonyl-(1-benzyl)-4-phenyl-1H-1,2,3-triazole
[0022] Under air, 1-phenylethynylphenylsulfide (0.2mmol, 42.0mg) was dissolved in chloroform (2mL), and benzyl azide (0.3mmol, 40.2mg) and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), stirred the reaction mixture at 40°C, reacted for 12h, then added m-chloroperoxybenzoic acid (0.6mmol, 103.5mg), reacted at room temperature for 3h, and separated by column chromatography after the reaction to obtain 62mg of a yellow solid product , yield 80%.
[0023]
[0024] Mp=139-141°C. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.78(d, J=8.0Hz, 2H), 7.58(t, J=8.0Hz, 1H), 7.52(t, J=8.0Hz, 1H), 7.46-7.38(m, 4H) ,7.21(t,J=8.0Hz,1H),7.19-7.13(m,2H),6.84-6.79(m,4H),4.34(t,J=8.0Hz,2H),3.12(t,J=8.0 Hz,2H). 13 C NMR (100MHz, CDCl 3 ): δ145.2, 140.9, 139.6, 136.4, 133.5, 130.5, 129.8, 129.0, 128.8, 128.6, 128.6, 127.8, 127.1, 124.1, 49.9, 36.3. HRMS (ESI-TOF) m / z calcd for C 22 h 19 N 3 o 2 S(M+Na) + 412.1090,foun...
Embodiment 2
[0025] Example 2: Preparation of 5-benzenesulfonyl-(1-benzyl)-4-p-methoxyphenyl-1H-1,2,3-triazole
[0026] Under air, 1-p-methoxyphenylethynylphenylsulfide (0.2mmol, 48.0mg) was dissolved in chloroform (2mL), and then benzyl azide (0.3mmol, 40.2mg) and [Rh(CO ) 2 Cl] 2 (0.005mmol, 1.9mg), stirred the reaction mixture at 40°C, reacted for 12h, then added m-chloroperoxybenzoic acid (0.6mmol, 103.5mg), reacted at room temperature for 3h, and separated by column chromatography after the reaction to obtain a colorless liquid product 61 mg, yield 75%.
[0027]
[0028] 1 HNMR (400MHz, CDCl 3 , TMS): δ7.57(d, J=8.0Hz, 2H), 7.42(t, J=8.0Hz, 1H), 7.35-7.33(m, 5H), 7.18-7.12(m, 4H), 6.96( d, J=12.0Hz, 2H), 6.06(s, 2H), 3.88(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ160.7, 150.1, 140.0, 134.7, 133.9, 131.8, 131.5, 128.9, 128.8, 128.5, 128.1, 127.0, 121.1, 113.6, 55.3, 54.5. HRMS (ESI-TOF) m / z calcd for C 22 h 19 N 3 o 3 S(M+Na) + 428.1039, found 428.1043.
Embodiment 3
[0029] Example 3: Preparation of 5-benzenesulfonyl-(1-benzyl)-4-p-bromophenyl-1H-1,2,3-triazole
[0030] Under air, 1-p-bromophenylethynylphenylsulfide (0.2mmol, 57.6mg) was dissolved in chloroform (2mL), and benzyl azide (0.3mmol, 40.2mg) and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), stirred the reaction mixture at 40°C, reacted for 12h, then added m-chloroperoxybenzoic acid (0.6mmol, 103.5mg), reacted at room temperature for 3h, and separated by column chromatography after the reaction to obtain 64mg of white solid product , yield 71%.
[0031]
[0032] Mp=141-143°C. 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.57(dd,J=12.0,8.0Hz,4H),7.44(t,J=8.0Hz,1H),7.36-7.34(m,5H),7.20-7.13(m,4H), 6.06(s,2H). 13 C NMR (100MHz, CDCl 3 ): δ149.0, 139.7, 134.5, 134.2, 132.5, 131.7, 131.4, 129.0, 128.9, 128.6, 128.1, 127.8, 127.0, 124.3, 54.5. HRMS (ESI-TOF) m / z calcd for C 21 h 16 BrN 3 o 2 S(M+Na) +476.0039,found 476.0042.
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