Sodium Iodide → N-(3-Iodophenyl)maleimide

HRID 982157Notes

Reaction equation

HRID 982157 reaction equation
[I-:1].[Na+].C([Sn](CCCC)(CCCC)[C:8]1[CH:9]=[C:10]([N:14]2[C:18](=[O:19])[CH:17]=[CH:16][C:15]2=[O:20])[CH:11]=[CH:12][CH:13]=1)CCC.CC1C=CC(S(NCl)(=O)=O)=CC=1.S(=O)(O)[O-].[Na+]>O.C(Cl)Cl.CCOC(C)=O.CCCCCC>[I:1][C:8]1[CH:9]=[C:10]([N:14]2[C:18](=[O:19])[CH:17]=[CH:16][C:15]2=[O:20])[CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 31388TosylchloramideHCID 20069270HCID 20069270, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 126214N-(3-Iodophenyl)maleimideYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirred solution of sodium iodide (32 mg, 0.21 mmol) in H2O (100 μL), was added N-(m-tri-n-butylstannylphenyl)maleimide as described above (0.1 g, 0.21 mmol) in CH2Cl2 (2 mL), followed by a solution of chloramine-T (59 mg, 0.21 mmol) in H2O (2 mL). Reaction progress was followed by TLC on silica gel GHLFC plates (EtOAc/hexane, 1:3), starting material 4 Rf 0.65. The reaction mixture was stirred at room temperature for 30 minutes. The mixture initially turned yellow from the formation of I+. The solution rapidly became lighter until a colorless solution resulted. To this was added 2 mL of 5% aqueous sodium bisulfite and the resulting mixture was extracted with dichloromethane (4×10 mL). The dichloromethane extracts were dried (MgSO4), and the solvent was removed in vacuo to give the desired product N-(m-iodophenyl)maleimide (60 mg/ 95%): TLC (EtOAc/hexane, 1:3) Rf 0.42; mp 154°-155° C. 1H NMR (CDCl3), δ); 7.1-7.7 (multiplets, 4H, 4 aryl CH); 6.8 (singlet, 2H, 2 CHC=O).

Workup

  1. customReaction progress
  2. customresulted
  3. extractionthe resulting mixture was extracted with dichloromethane (4×10 mL)
  4. dry with materialThe dichloromethane extracts were dried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-156c9ca53f824a52be83767621e9f089
Source dataset
uspto-grants-1991_02
Patent number
US04994557

Reaction notes

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