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Chemistry
Heterocyclic Building Blocks
Thiazoles
N1-((2-Chlorothiazol-5-yl)methyl)ethane-1,2-diamine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Thiazoles
Amines Chlorides

[ CAS No. 167776-64-9 ] {[proInfo.proName]}

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CAS No. :167776-64-9 MDL No. :
Formula : C6H10ClN3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 191.68 Pubchem ID :-
Synonyms :

Safety of [ 167776-64-9 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 167776-64-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 167776-64-9 ]

[ 167776-64-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 105827-91-6 ]
  • [ 107-15-3 ]
  • [ 167776-64-9 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate; In acetonitrile; at 0 - 20℃; for 8h; (1): Synthesis of N1-((2-chlorothiazol-5-yl)methyl)ethane-1,2-diamine To a stirred solution of 0.03mol of potassium carbonate and 10ml (0.15mol) of ethylenediamine in a 50ml of flask placed in an ice bath, 0.03mol of <strong>[105827-91-6]2-chloro-5-(chloromethyl)thiazole</strong> dissolved in 15ml of acetonitrile was added dropwise and slowly. After addition, the ice bath was removed and then the mixture was stirred for 8 hours at room temperature. After the reaction was stopped, a large amount of water was added to dissolve potassium carbonate and ethylenediamine, and the mixture was extracted with dichlormethane. The lower organic phase was collected, dried, and evaporated to dryness. The obtained product was yellow oily liquid in 70% yield. GC MS (m/s) 191 (21) M+, 132(100).
70% With potassium carbonate; In acetonitrile; at 0 - 20℃; for 8h; (1): Synthesis of N1-((2-chlorothiazol-5-yl)methyl)ethane-1,2-diamine To a stirred solution of 0.03mol of potassium carbonate and 10ml (0.15mol) of ethylenediamine in a 50ml of flask placed in an ice bath, 0.03mol of <strong>[105827-91-6]2-chloro-5-(chloromethyl)thiazole</strong> dissolved in 15ml of acetonitrile was added dropwise and slowly. After addition, the ice bath was removed and then the mixture was stirred for 8 hours at room temperature. After the reaction was complete, a large amount of water was added to dissolve potassium carbonate and ethylenediamine, and the mixture was extracted with dichloromethane. The lower organic phase was collected, dried, and evaporated to dryness. The obtained product was yellow oily liquid in 70% yield. GC MS (m/s) 191 (21) M+, 132(100).
70% With potassium carbonate; In acetonitrile; at 0 - 20℃; for 8h; EXAMPLE 7; Synthesis of 1-((2-chlorothiazol-5-yl)methyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol (compound 12)(1): Synthesis of N1-((2-chlorothiazol-5-yl)methyl)ethane-1,2-diamine To a stirred solution of 0.03 mol of potassium carbonate and 10 ml (0.15 mol) of ethylenediamine in a 50 ml of flask placed in an ice bath, 0.03 mol of <strong>[105827-91-6]2-chloro-5-(chloromethyl)thiazole</strong> dissolved in 15 ml of acetonitrile was added dropwise and slowly. After addition, the ice bath was removed and then the mixture was stirred for 8 hours at room temperature. After the reaction was complete, a large amount of water was added to dissolve potassium carbonate and ethylenediamine, and the mixture was extracted with dichloromethane. The lower organic phase was collected, dried, and evaporated to dryness. The obtained product was yellow oily liquid in 70% yield.GC MS (m/s) 191 (21) M+, 132 (100).
Reference： [1]Synlett,2015,vol. 26,p. 393 - 403
[2]Patent: EP1826209,2007,A1 .Location in patent: Page/Page column 10
[3]Patent: EP1997820,2008,A1 .Location in patent: Page/Page column 12
[4]Patent: US2009/111847,2009,A1 .Location in patent: Page/Page column 8
[5]Tetrahedron,2009,vol. 65,p. 10377 - 10382
[6]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 951 - 957
[7]Heteroatom Chemistry,2009,vol. 20,p. 418 - 424
[8]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 901 - 906
[9]Monatshefte fur Chemie,2010,vol. 141,p. 1117 - 1122
[10]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1136 - 1142
  • 2
  • [ 167776-64-9 ]
  • [ 13623-94-4 ]
  • [ 105828-97-5 ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 8h; Reflux;
56% With acetic acid In ethanol at 80 - 90℃; for 4h; Heating / reflux; 7.2 (2): Synthesis of 1-((2-chlorothiazol-5-yl)methyl)-2-(nitromethylene)-1-imidazolidine 2.5g (0.0178mol) of 1,1-dimethylthio-2-nitroethene, 3.3g (0.0178mol) of N1-((2-chlorothiazol-5-yl)methyl)ethane-1,2-diamine were dissolved in 15ml of ethanol. The resulting mixture was refluxed at 80-90 °C for 4 hours. The mixture was then cooled to educe solid, concentrated, filtrated and dried to give a light yellow powder in 56% yield. GC MS(m/s) 226 (24), 132(100), 77(9).
56% In ethanol at 80 - 90℃; for 4h; 7.2 (2): Synthesis of 1-((2-chlorothiazol-5-yl)methyl)-2-(nitromethylene)-1-imidazolidine 2.5 g (0.0178 mol) of 1,1-dimethylthio-2-nitroethene, 3.3 g (0.0178 mol) of N1-((2-chlorothiazol-5-yl)methyl)ethane-1,2-diamine were dissolved in 15 ml of ethanol. The resulting mixture was refluxed at 80-90° C. for 4 hours. The mixture was then cooled to educe solid, concentrated, filtrated and dried to give a light yellow powder in 56% yield.GC MS (m/s) 226 (24), 132 (100), 77 (9).
In ethanol for 4h; Reflux;
In ethanol Reflux;
In ethanol
In ethanol Reflux;

Reference： [1]Fan, Yefeng; Liu, Song; Chen, Nanyang; Shao, Xusheng; Xu, Xiaoyong; Li, Zhong [Synlett, 2015, vol. 26, # 3, p. 393 - 403]
[2]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - EP1997820, 2008, A1 Location in patent: Page/Page column 13
[3]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2009/111847, 2009, A1 Location in patent: Page/Page column 8-9
[4]Location in patent: experimental part Wang, Kewei; Qian, Xuhong; Cui, Jingnan [Tetrahedron, 2009, vol. 65, # 50, p. 10377 - 10382]
[5]Location in patent: scheme or table Shao, Xusheng; Li, Zhong; Qian, Xuhong; Xu, Xiaoyong [Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 3, p. 951 - 957]
[6]Location in patent: scheme or table Wang, Kewei; Qian, Xuhong; Cui, Jingnan [Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1117 - 1122]
[7]Shao, Xusheng; Huang, Xinglong; Shi, Qian; Li, Zhong; Tao, Liming; Song, Gonghua [Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1136 - 1142] Zhang, Xiao; Wang, Yiping; Xu, Zhiping; Shao, Xusheng; Liu, Zewen; Xu, Xiaoyong; Maienfisch, Peter; Li, Zhong [Journal of Agricultural and Food Chemistry, 2021, vol. 69, # 10, p. 3005 - 3014]
  • 3
  • [ 167776-64-9 ]
  • [ 17823-69-7 ]
  • [ 1327339-16-1 ]
Reference： [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 901 - 906

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