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(N-aryl sulfinyl)sulfonyl hydrazide and preparation method thereof

An arylsulfinyl and chloroarylsulfinyl sulfonimide technology is applied in the field of (N-arylsulfinyl) sulfonyl hydrazide and its preparation, and can solve the problems of sulfinic acid preparation problems and the like

Active Publication Date: 2016-06-29
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sulfonyl hydrazide can also be prepared conveniently by the hydrosulfonylation of azodicarboxylate with sulfinic acid (W.Y.Chan, C.Berthelette, Tertahedron Lett.,2002, 43, 4537; J.W.Wen ,W.Wei,D.SYang,Y.F.Fan,L.L.Fu,H.Wang,Synth.Commun.,2015,45,1574.), but the preparation of raw material sulfinic acid is a difficult problem

Method used

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  • (N-aryl sulfinyl)sulfonyl hydrazide and preparation method thereof
  • (N-aryl sulfinyl)sulfonyl hydrazide and preparation method thereof
  • (N-aryl sulfinyl)sulfonyl hydrazide and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] N' -methyl- N' -Phenyl- N -(Benzenesulfinyl)-4-toluenesulfonylhydrazide 1a

[0039] Will N -Methylaniline (160mg, 1.5mmol) and N -chlorine- N -(4-Toluenesulfonyl)benzenesulfinamide (1.25mmol, 410mg) was mixed in 10mL of dry dichloromethane and stirred at room temperature for 2h. After the solvent was removed by spin, the product was separated by a silica gel column to obtain a colorless oil. 220mg, 44%. 1 HNMR (400MHz, CDCl 3 )δ7.91(d, J=8.3Hz,2H),7.77–7.70(m,2H),7.60(t, J =7.4Hz,1H),7.47(t, J =7.8Hz,2H),7.34–7.28(m,3H),7.26(s,1H),7.24(s,1H),7.19–7.12(m,2H),3.29(s,3H),2.39(s, 3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ142.8, 140.8, 140.4, 136.5, 133.5, 129.2, 129.1, 129.0, 128.2, 128.0, 127.7, 126.7, 39.5, 21.5. IR (film, KBr) v cm -1 1595,1492,1447,1320,1271,1155,1108,1089,1074.ESI-HRMS[M+H] + calcforC 20 h 21 N 2 o 3 S 2 401.0988,found 401.0993.

Embodiment 2

[0041] N',N' -Dibenzyl- N -(Benzenesulfinyl)-4-toluenesulfonylhydrazide 1b

[0042] According to the method described in Example 1, using dibenzylamine as raw material, to obtain N',N' -Dibenzyl- N -(Benzenesulfinyl)-4-toluenesulfonylhydrazide, colorless oil, 280mg, 46%. 1 HNMR (400MHz, CDCl3) δ7.94–7.82 (m, 4H), 7.58 (t, J =7.5Hz,1H),7.46(t, J =7.8Hz,2H),7.41–7.32(m,2H),7.28–7.24(m,2H),7.21–7.14(m,4H),7.03–6.96(m,4H),4.44(s,4H), 2.40(s,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ142.7, 140.8, 139.3, 134.6, 133.4, 129.2, 129.1, 128.9, 128.4, 127.9, 127.6, 126.7, 51.0, 21.5. IR (film, KBr) v cm -1 1599,1496,1455,1447,1320,1257,1155,1109,1088,1074.ESI-HRMS[M+H] + calcforC 27 h 27 N 2 o 3 S 2 491.1458,found 491.1460.

Embodiment 3

[0044] N -(Indoline-1-yl)- N -(Benzenesulfinyl)-4-toluenesulfonamide 1c

[0045] According to the method described in Example 1, use indoline as raw material to obtain N -(Indoline-1-yl)- N -(Benzenesulfinyl)-4-toluenesulfonamide, colorless oil, 33mg, 65%. 1 HNMR (400MHz, CDCl 3 )δ7.90(d, J =8.3Hz,2H),7.85(dd, J =8.4,1.0Hz,2H),7.61–7.53(m,1H),7.50(d, J =8.1Hz,1H),7.43(dd, J =10.8,4.9Hz,2H),7.25(d, J =8.8Hz,2H),7.14(t, J =7.7Hz,1H),7.08(d, J =7.0Hz,1H),6.99(td, J =7.4,0.7Hz,1H),4.23–4.12(m,1H),4.05–3.94(m,1H),2.94(ddd, J =16.3,9.7,6.9Hz,1H),2.84(ddd, J =16.3,9.7,6.9Hz,1H),2.39(s,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ142.9, 141.1, 140.5, 136.6, 133.8, 132.4, 129.193, 129.185, 127.7, 127.1, 126.8, 125.2, 124.5, 115.9, 51.4, 27.8, 21.5. IR (film, KBr) v cm -1 1600,1477,1460,1322,1266,1156,1112,1089.ESI-HRMS[M+H] + calcforC 21 h 21 N 2 o 3 S 2 413.0988,found 413.0987.

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Abstract

The invention provides a (N-aryl sulfinyl)sulfonyl hydrazide compound and a preparation method thereof. N-chloro-aryl sulfinyl sulfimide and secondary amine are subjected to direct condensation, and the corresponding (N-aryl sulfinyl)sulfonyl hydrazide compound is obtained. According to the preparation method of the compound, the raw materials are simple and easy to obtain, and operation is convenient. The obtained compound is a very important organic intermediate and drug intermediate and has various biological activities.

Description

Technical field [0001] The present invention is an organic synthetic technology field, which involves (N-Fenyl sulfonyl) sulfonyl and its preparation methods. Background technique [0002] Sulfonyl is a very important organic intermediate, which is widely used in the field of pharmaceutical chemistry and synthetic chemistry.In pharmaceutical chemistry, sulfonic acid shows many biological activity, such as inhibiting cell growth (h.a.seow, p.g.penkethandk.shyam, s, rockwellanda.c.sartorelli, Proc.natl.acad.sci., 2005, 102,9282; a.kamal, m.n.a.khan, k.s.redddyandk.rohini, Bioorg.Med.chm. , 2011,15,1004; P.G.penkth, K, Shyam, R.P.BAUMANN, J.S.RMACK, T.P.BRENTANDA.K.SARTORELLI,, Cancerchmother.pharmacol., 2004,24,568; J.P.Power, D.E.PIPER, Y.LI, v.Mayorga, J.ANZOLAANDJ.M.CHen, J.med.chm., 2006,49,1034.), Antibacterial (A.M.AL-AZZAWIANDM.S.A.razzak, J.Pharm.sci., 2011,2,124.), Anti -inflammatory and analgesic (S.M.SONDHI, M, Dinodiaanda.kumar, Bioorg.Med.chm., 2006,14,4657; a.lgnat, v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/06C07D209/08C07D217/08
CPCC07C313/06C07D209/08C07D217/08
Inventor 许家喜杨占会
Owner BEIJING UNIV OF CHEM TECH