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Chemical Structure| 90585-26-5 Chemical Structure| 90585-26-5

Structure of 90585-26-5

Chemical Structure| 90585-26-5

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Product Details of [ 90585-26-5 ]

CAS No. :90585-26-5
Formula : C9H10INO
M.W : 275.09
SMILES Code : CC(N(C1=CC=CC=C1I)C)=O

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Application In Synthesis of [ 90585-26-5 ]

* 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 [ 90585-26-5 ]

[ 90585-26-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 19591-17-4 ]
  • [ 74-88-4 ]
  • [ 90585-26-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: The procedure consists of two steps. First, to a stirred, cooled (0-5C) solution of 2-bromoaniline (2.190g, 10mmol) and Et3N (1.113g, 1.55ml, 11mmol) in 20ml of dry THF, a solution of an appropriate acyl chloride (10mmol) in 5ml of dry THF was added dropwise within 10min. Then the ice bath was removed and the mixture was stirred vigorously for 30min at room temperature. Then, solid Et3NHCl was filtered off and washed with THF (3×5ml). The resulting organic fractions were combined and THF was removed under reduced pressure to yield crude amides. Recrystallization from hexane/CHCl3 and drying in vacuum afforded the analytically pure intermediate compounds: N-(2-bromophenyl)acylamides. In the second step, to a stirred suspension of NaH (0.132g; 5.5mmol) in 5ml of dry THF at 0C the respective amide (5mmol) dissolved in 10ml of THF was added dropwise within 10min. The reaction mixture was stirred until the solution became clear (30min, hydrogen gas evolved), and the solution of MeI (0.923g; 0.405ml; 6.5mmol) in 5ml of THF was added dropwise within 10min. The solution was warmed up to room temperature and stirred for 3-8h. Then, the reaction mixture was quenched with water (30ml). The resulting solution was extracted with ethyl acetate (3×20ml). Combined organic layers were washed with brine (1×20ml) and dried over Na2SO4. Ethyl acetate was removed under reduced pressure to give crude 1a-r. Recrystallization from hexane and drying in vacuum afforded analytically pure compounds 1a-r. In the case of (1n) and (1o), the same procedure was conducted but instead of MeI, ethyl bromide and benzyl bromide were respectively used. In the case of (1p), 2-bromopyridin-3-amine was used instead of 2 bromoaniline. In the case of (1a-Cl) and (1a-I), the same procedure was conducted but instead 2-bromoaniline, 2-chloro- and 2-iodoaniline were respectively used.
 

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